115 Things to Do in Boston for $10 or Less: October 2024
When:
Tuesday, Oct 01, 2024 9:00a -
Thursday, Oct 31, 2024 11:00p
Tuesday, Oct 01, 2024 9:00a -
Thursday, Oct 31, 2024 11:00p
Where:
Boston
Surrounding areas
Boston, MA
Admission:
$0+
Categories:
Animals, Art, Classes, Date Idea, Drinks, Farms, Festivals & Fairs, Food, Games, Good for Groups, History, Innovation, Kid Friendly, LGBTQ+, Meetup, Movies, Music, Nature, Nightlife, Outside, Party, Pet Friendly, Photoworthy, Seasonal, Shopping, Shows, Social Good, Sports & Active Life, University
Boo! It’s October which means it’s Halloween season all month long, my Boston friends. Welcome fall, spooky vibes, apple cider donuts, and pumpkin spice lattes as you explore the city and watch the streets fill with shades of red, orange, and yellow. Here’s your guide to all things cheap and free — 115 things to be exact! — to make the most of Boston’s bootiful change in seasons.
By Yelena Nicolle Salvador
When: Tue. 10/1
Where: South End
Cost: Free
Info: Come on over to SoWa and wander through the art galleries. Meet the artists and kick off October in full blown color as you get inspired by paintings, sculptures, and more.
2) J.P. Licks 25 Years Roasting Celebration & Artist Reception
When: Tue. 10/1
Where: Dorchester
Cost: Free
Info: J.P. Licks has officially been serving coffee for 25 years! It’s time to celebrate by heading over to Dorchester for a day full of family fun: games, prizes, and free samples of coffee. Don’t forget to try their new Frōjō product and enjoy their art gallery featuring art by J.P. employees.
3) Lalela Wines Free Public Tasting at the Urban Grape
When: Tue. 10/1
Where: Back Bay
Cost: Free
Info: Learn from the founders of South African wine brand, Lalela! They’ll be discussing the 400+ year history of winemaking in South Africa with some tastings of their new vinos. This is a great way to meet new friends and learn about wine!
When: Tue. 10/1
Where: Back Bay
Cost: Free
Info: Get creative and meet some friends at this cozy event by Trident. Bring your own embroidery, crochet, or knitting project, or even just a book to read, and say hello to your neighbor as you embrace the fall season with a candy apple milkshake and homey vibes.
5) Sketch Sesh
When: Tuesdays, starting 10/1
Where: Seaport
Cost: Free
Info: Come sketch for fun and learn some techniques at the Superette Courtyard with folks who are looking to get creative. Art supplies, music, and mini lessons are all included! Just bring yourself and some friends if you wish!
6) Barry’s Bootcamp at the Esplanade
When: Tuesdays, starting 10/1
Where: The Esplanade
Cost: Free
Info: Break a sweat as you feel the autumn breeze along the Esplanade. It’s the perfect weather to get your heart pumping with a beautiful view too.
7) Berklee Summer in the City Concert
When: Tuesdays, starting 10/1
Where: Back Bay
Cost: Free
Info: Head to Back Bay’s new Lyrik Plaza and enjoy live music presented by some of Boston’s up and coming talent as you explore the open-air space with greenery, stunning views, and of course, a whole lot of rhythm.
8) Coffee Tasting with New England Coffee
When: Wed. 10/2
Where: Downtown
Cost: Free
Info: Explore the world of coffee at Dewey Square Park! Come visit a coffee truck in honor of a belated National Coffee Day with free coffee tastings, coffee-themed games, and music.
9) Joker Folie a Deux Advanced Screening
When: Wed. 10/2
Where: Downtown
Cost: Free
Info: Come watch the new Joker sequel for free, featuring Lady Gaga as the new Harley Quinn! Costumes are encouraged and come early since seats are first come, first served.
10) Watch Wednesdays at The Anchor
When: Wednesdays, starting 10/2 - 10/30
Where: Charlestown
Cost: Free
Info: Watch a spooky film from “Scooby Doo” and “Ghostbusters” to “Hocus Pocus” and more as grab a drink and take in skyline views of Boston from Charlestown Naval Yard.
11) Dragula Watch Party at Aeronaut Somerville
When: Wednesdays, starting 10/2
Where: Somerville
Cost: $5
Info: Mother Monster is calling you to join the ultimate watch party with local drag performers. You’ll get to meet Dragula icons and enjoy brews with dashing company.
12) Yappy Hour at The Charles Hotel Courtyard
When: Wednesdays, starting 10/2 - 10/30
Where: Harvard Square
Cost: Free
Info: Bring your pups and meet new friends at Yappy Hour. Stay a while as you grab a free pet portrait and a “barkuterie” board. Have your furry friend enjoy a non-alcoholic puppy-friendly “beer,” “CharDOGnay,” and “ZinfinTAIL” too!
13) Free First Thursdays at the Isabella Stewart Gardner Museum
When: Thu. 10/3
Where: Fenway
Cost: Free
Info: Head to one of the most beautiful museums in Boston for free! Wander through floors of art from all over the world and a stunning indoor courtyard with seasonal flowers. If you weren’t able to reserve your free ticket, get there early for a chance at a walk-up reservation.
When: Thu. 10/3 - Sat. 10/5
Where: Charlestown
Cost: Free
Info: Head to The Anchor for free play basketball, watch some college basketball, join the NBA2K Tournament, and enjoy a football watch party. There will be food, music, games, and so much more.
When: Thursdays, starting 10/3
Where: West End
Cost: Free
Info: Head to this museum on Thursdays to relax and enjoy waterfront views. Explore the galleries of contemporary art and feel inspired!
16) FOUND on Canal Vintage Markets: TD Pre Concert Series
When: Thu. 10/3 & Fri. 10/11
Where: West End
Cost: Free
Info: Look for your next treasure to elevate your outfit before the Sabrina Carpenter and Billie Eilish concerts! Shop from 30 of Boston’s best vintage vendors right outside TD Garden.
17) Watercolor Workshops at Lyrik Plaza
When: Thursdays, starting 10/3
Where: Back Bay
Cost: Free
Info: As you explore the new Back Bay piazza, enjoy a watercolor workshop for free where you can paint whatever you wish from the Boston skyline to your favorite animal. Supplies will be provided and Ashley, a Boston-based painter, will be there to guide you!
When: Thursdays, starting 10/3 - 10/24
Where: The Greenway
Cost: Free
Info: Enjoy spooky-themed flicks on The Greenway now that Halloween season is here and nights are falling upon us a bit earlier. Bring a blanket and enjoy free popcorn, swag, and giveaways at this weekly event.
19) Fashionably LATE Fashion Shows at The Liberty
When: Thursdays, starting 10/3 - 10/27
Where: Back Bay
Cost: Free
Info: Head to the Liberty Hotel for a weekly fashion show featuring pieces by local designers. Models will strut their stuff through the lobby, on escalators, and through the crowds as you get inspired by their fall looks.
20) Venture Cafe Thursday Gatherings
When: Thursdays, starting 10/3
Where: Cambridge
Cost: Free
Info: Connect with entrepreneurs, creators, investors, academics, students, visionaries, and so much more at this free networking event. You’ll be able to meet new folks so you can collaborate on your next project or feel inspired to start a new one!
When: Fri. 10/4
Where: South End
Cost: Free
Info: Get inspired by local artists and explore the magic of SoWa at their First Friday event where you can visit the open galleries in the area.
When: Fri. 10/4
Where: South End
Cost: Free
Info: Head to Dray for the first Friday of Sober October where you can learn how to mix your own mocktails with Kevvnation for free! Meet new friends and have fun at this class.
23) Coworking Day at The Substation
When: Fri. 10/4
Where: Roslindale
Cost: Free
Info: Ready to switch up your WFH space? Check out the Substation for their free monthly coworking day. Enjoy free coffee, pastries, snacks, and wifi as you get productive!
24) Grrrl Talk @ Remnant Satellite
When: Fri. 10/4
Where: Cambridge
Cost: Free
Info: Calling all the ladies! Here’s your chance to meet new girlfriends at this event made by and for women. Come drink, talk, and dance to classic vinyl faves.
When: Fri. 10/4, Wed. 10/16, & Mon. 10/28
Where: Roxbury
Cost: Free
Info: October is known for its month-long event called Inktober where people all over the world celebrate creativity. Enjoy fun prompts that will inspire you to draw, craft, and more. At these events, you can meet new friends and cheer others on as you spend some quality time making new art!
26) Live Music Fridays at The Berkeley
When: Fridays, starting 10/4
Where: Back Bay
Cost: Free
Info: Head to this new restaurant in Back Bay and enjoy some live music on their bar-side terrace. It’s the perfect way to kick off your weekend and cool off after a busy week.
27) Summer Rooftop DJ Weekends @ Sam Adams
When: Fri. 10/4 - Sat. 10/5
Where: Downtown
Cost: Free
Info: It’s the final weekend of rooftop DJ weekends at Sam Adams. Say goodbye to summer with a brew in hand and views of the city as you bump to DJ tunes.
28) Law & Order Station: Fan Experience
When: Fri. 10/4 - Sat. 10/5
Where: Downtown
Cost: Free
Info: This experience is for all my Law & Order fans. A free pop-up experience is coming to Faneuil Hall with photo ops, a complimentary Kane’s donut, and a free Stella Blue coffee. Walk through three decades of L&O history and get ready for the new seasons dropping soon.
29) HONK! Festival of Activist Street Bands 2024
When: Fri. 10/4 - Sun. 10/6
Where: South End
Cost: Free
Info: Somerville’s three-day musical festival returns for its 19th year. With more than 25 bands, you’ll be able to listen to a wide variety of genres and dance. Plus, listen to discussions featuring musicians who are supporting local organizations and playing for a cause. Don’t forget to catch their famous parade too!
30) Saturday Screening of ‘Hocus Pocus’
When: Sat. 10/5
Where: Brighton
Cost: Free
Info: Kick off spooky season with the ultimate cult-classic movie, ‘Hocus Pocus,’ at the Brighton Branch of the Public Library. It’s the perfect way to get in the Halloween spirit!
31) Fall Fest at Kendall/MIT Open Space
When: Sat. 10/5
Where: Kendall Square
Cost: Free
Info: Welcome fall at this family-friendly celebration. Enjoy free hot cocoa and chai, lawn games, live music, and face painting.
32) Boston Public Library Book Sale
When: Sat. 10/5
Where: Back Bay
Cost: Free
Info: Admission is free to this treasure hunters’ paradise. Find books, CDs, DVDs, and so much more during the Boston Public Library’s big fall sale where items cost between $1-2! Proceeds support the BPL too.
33) Spooky Saturday at Urban Park
When: Sat. 10/5
Where: Kendall
Cost: Free
Info: Head to the secret rooftop park for the ultimate spooky celebration. Make your own flower bouquet, watch a cooking demo, and pick your own pumpkin from the mini pumpkin patch!
34) Trident Booksellers 40th Anniversary Party
When: Sat. 10/5
Where: Back Bay
Cost: Free
Info: This beloved local staple is turning 40! Come celebrate this big birthday featuring free food samples off the menu, free books, free fortunes, and a memorabilia showcase at the brand-new event space, The Stacks!
35) Fall Festival at the Lawn on D
When: Sat. 10/5
Where: Seaport
Cost: Free
Info: Get ready for the ultimate autumn party at the Lawn on D! Enjoy free apps and snacks as you shop at the pop-up market, meet some cute and furry animals, watch aerial and stilt performers, and participate in glow-in-the-dark activities when the sun goes down.
When: Sat. 10/5
Where: Back Bay
Cost: Free
Info: Take part in this interactive live music showcase as you watch two pianists battle it out as they play a mix of rock and other audience faves. Come sing, dance, and crown the piano winner!
When: Sat. 10/5
Where: Assembly Row
Cost: Free
Info: Head to Club Volo for their Pickleballtoberfest celebration. Enjoy pickleball, of course, as well as fall-themed snacks and drinks, a stein holding challenge, a costume contest, and more!
38) Beginner Charleston Lesson
When: Sat. 10/5
Where: Cambridge
Cost: Free
Info: If you always wanted to learn to dance, come to this absolute beginner class and start your journey with swing! You’ll get to participate in a Charleston workshop where you’ll practice basic footwork and other fun moves.
39) Quincy’s Food Truck and Music Festival
When: Sat. 10/5
Where: Quincy
Cost: Free
Info: Find your next favorite food from over 30 food and dessert trucks in Quincy. There will be drinks and live entertainment for adults and kiddos alike featuring disco and funk music, as well as magic shows and more.
40) Welcome Fall Grand Tasting
When: Sat. 10/5 - Sun. 10/6
Where: Back Bay
Cost: Free
Info: Get cozy with some new friends and delicious wine. Enjoy this grand tasting of 50 wines featuring medium bodied white wines and heavier reds. Don’t forget to RSVP to save your spot.
When: Sat. 10/5 - Sun. 10/6
Where: Jamaica Plain
Cost: Free
Info: Come discover the beauty of caterpillars! Researchers and staff will have hundreds of caterpillars, cocoons, and fun facts for you and your friends as you wander through this pop-up exhibit and have a chance at using special magnifying equipment.
42) 25th Annual Roxbury Open Studios Art Festival
When: Sat. 10/5 - Sun. 10/6
Where: Roxbury
Cost: Free
Info: Meet the talented artists of Roxbury. At this art festival, you’ll be able to experience a multimedia, multicultural, and multigenerational community celebration as you learn more about local creatives.
43) Arcade Night at The Anchor
When: Saturdays, starting 10/5 - 10/26
Where: Charlestown
Cost: Free
Info: Join the ultimate gaming party. Participate in the NBA 2K Tournament or simply enjoy some casual gaming with friends and neighbors by playing some Mario Kart or Mario Party. You’ll be along the water and enjoy sunset views while you participate in some friendly competition.
When: Saturdays, starting 10/5 - 10/26
Where: Back Bay
Cost: Free
Info: It’s the last month of this beloved market’s season. Don’t forget to stop by, meet some local artists, and support some small businesses!
45) Pickleball Day Party at Club Volo
When: Saturdays, starting 10/5 - 10/26
Where: Somerville
Cost: Free
Info: Head to Club Volo in Assembly Row for fun games and some sunshine. The first 25 people get a free drink and you’ll be able to play some pickleball, flip cup, and bocce! Head on over before it gets too cold!
46) 45th Annual Harvard Square Oktoberfest
When: Sun. 10/6
Where: Harvard Square
Cost: Free
Info: Enjoy street food and multiple beer garden pop-ups around Harvard Square. It’s the ultimate Oktoberfest celebration with live music on multiple stages, artist stalls, free giveaways, and family-friendly activities.
47) 3rd Annual Filipino American Festival at Harvard Square
When: Sun. 10/6
Where: Harvard Square
Cost: Free
Info: Learn about Filipino culture through vibrant cuisine, live music, and traditional dance performances. You’ll be able to meet folks within the community and feel like you’re part of the family at this community celebration.
48) Open House at the Colonial Society of Massachusetts
When: Sun. 10/6
Where: Beacon Hill
Cost: Free
Info: Explore this historical building that was built in the early 1800’s in the heart of Boston . Look at 19th century antique furniture and art collections across two floors of the Colonial Society of Massachusetts headquarters.
49) 20s & 30s Fall Foliage Walk - Arnold Arboretum
When: Sun. 10/6
Where: Jamaica Plain
Cost: Free
Info: Meet new friends and take in the beauty of Boston’s fall foliage with folks who are looking to build a community in Boston. This is the perfect way to meet others and explore Boston in its best season.
50) Brighton Bazaar’s How Bazaar! Expo
When: Sun. 10/6
Where: Brighton
Cost: Free
Info: The folks behind the beloved Brighton Bazaar have a debut event: How Bazaar! Find over 100 vendors who will be selling out-of-the-box, freaky, creepy, spooky oddities – you’ll definitely find your next treasure that will get people’s attention at this fun market!
When: Sundays, starting 10/6
Where: Charlestown
Cost: Free
Info: Get your voice ready and wear your favorite Pats merch as you cheer on the New England Patriots at the Anchor. With waterfront views, light bites, and alcoholic bevs, you’ll have lots of fun with your neighbors and feel the true NE spirit.
52) SoWa Open Market
When: Sundays, starting 10/6 - 10/27
Where: South End
Cost: Free
Info: It’s the last month of the SoWa Open Market season. Find your next gift, grab a snack from a food truck, play lawn games, and more at one of the largest open-air markets in Boston.
When: Sundays, starting 10/6
Where: South End
Cost: Free
Info: The perfect way to prepare for your upcoming week is to have a laugh. Test out your new standup routine or just come enjoy a drink while you have a listen. It’ll be a great time at GrandTen Distilling.
54) Rainbow Tales: LGBTQIA+ Storytelling
When: Mon. 10/7
Where: West End
Cost: Free
Info: Stop by and support the queer community of Boston at the Museum of Science. At this event, you’ll hear stories that amplify the voices of LGBTQIA+ folks and that center on diversity, gender identity, self expression, hope, and more.
55) Sugar Skull Paint Party @ The Anchor
When: Tue. 10/8
Where: Charlestown
Cost: Free
Info: Time to paint with an incredible view! Watch the sunset over the Boston skyline and the water as you design your own sugar skull – perfectly in theme with Halloween.
56) GBH Jazz Night featuring Kristalis Sotomayor
When: Thu. 10/10
Where: Back Bay
Cost: Free
Info: Listen to Latin rhythms fused with modern jazz at the monthly GBH Jazz Nights that showcase jazz talent from the Greater Boston area. This month’s lead is Puerto Ricon flutist, Kristalis Sotomayor.
57) Mariposa After Hours Concert
When: Thu. 10/10
Where: Central Square
Cost: Free
Info: Head to Mariposa Bakery at night for some live music presented by your favorite local baristas. Enjoy sounds by bands like Wayside Sounds, Silly Band, and Super Pink, as you enjoy some fall drinks and pastries.
58) Fall Fest Thursdays at the Loring Greenough House
When: Thursdays, starting 10/10 - 10/24
Where: South End
Cost: Free
Info: Thursdays on the Lawn at the Loring Greenough House just got a fall twist. Bring a picnic, enjoy the fall colors and the cool breeze, and sip on a drink from the pop-up beer garden by HIVE.
59) Friday Night at the Movies - ‘Whatever Happened to Baby Jane?’
When: Sat. 10/12
Where: Jamaica Plain
Cost: $7
Info: It’s the final outdoor movie night at the Loring Greenough House. Enjoy this black and white campy horror classic – the perfect way to get in the Halloween spirit.
60) Apple Booze Bash
When: Sat. 10/12
Where: Everett
Cost: Free
Info: Time to party and celebrate the wonderful apple. Munch on apple cider donuts, grab a meal from a food truck, enjoy spiked cider flights and other booze, and listen to live music. Plus, kids can enjoy free face painting, tattoos, and stickers.
When: Sat. 10/12
Where: Southie
Cost: Free
Info: It’s an Oktoberfest celebration for all ages! Dance to live music, sip on a German beer, play some family-friendly games, munch on some yummy food, and take part in some ax throwing.
62) Karaoke Night Hosted by DJ Matty
When: Sat. 10/12
Where: Dorchester
Cost: Free
Info: Keep yourself hydrated at Dorchester Brewing as you show off your singing skills during their karaoke night. It’s the perfect way to bond with a friend and sing your heart out.
63) Boston Women’s Market at Assembly Row
When: Sat. 10/12
Where: Somerville
Cost: Free
Info: Shop local and shop small by stopping by Assembly Row with over 30 vendors. Plus, you can bring your puppers and your kids to enjoy lawn games and more along the market area.
64) Proud to be a ___ Day Party: Fundraiser for Transgender Emergency Fund
When: Sat. 10/12
Where: Downtown
Cost: Free
Info: Head to Sam Adams Downtown to celebrate the release of their 4th annual Proud To Be __ brew in honor of National Coming Out Day. It’s all about pride so come sip, dance, and enter some giveaways.
65) Fall Vintage Clothing Pop-Up
When: Sat. 10/12 & Sat. 10/19
Where: Somerville
Cost: Free
Info: It’s a back-to-back Saturday event at Time Out where you can hint for your next treasure from over 40 vintage sellers. Grab a bite to eat or a drink to sip on as you shop local!
66) $5 Ferry Weekend to Spectacle Island
When: Sat. 10/12 - Mon. 10/14
Where: Boston Harbor Islands
Cost: Free
Info: Celebrate the end of the Boston Harbor Islands National and State Park 2024 season with cheap ferry tickets to Spectacle Island. Bring a picnic and a jacket, and come explore this hidden gem of Boston as you enjoy ocean views and wildlife!
When: Saturdays, starting 10/12 - 10/26
Where: Charlestown
Cost: Free
Info: Cheer on the Fighting Irish as Notre Dame competes against opponents on the big screen. Enjoy waterfront views, cold brews, and house-smoke specials as you watch!
68) Boston Landing’s Annual Fall Crawl
When: Sun. 10/13
Where: Brighton
Cost: Free
Info: This family-event was rescheduled for October, which makes it even more perfect to welcome fall. Enjoy pumpkin hoisting, stein hoisting, fall-themed food and bevs, a live band, seasonal crafts, and so much more. There’s something for all ages.
69) 9th Curated Vintage Market at Bow
When: Sun. 10/13
Where: Somerville
Cost: Free
Info: Calling all treasure hunters! The beloved Curated Vintage Market is back at Bow for its 9th installment with over 80 vintage vendors from across New England. Get ready to find your next statement piece at this community event.
70) Queer Babes Who Walk: Cambridge
When: Sun. 10/13
Where: Cambridge
Cost: Free
Info: Get ready to walk with new friends through this Pink Pony Club community. To all queer women and non-binary folks, here’s a place for you to meet others, talk, and enjoy the outdoors.
71) Books and Brews: A Spooky Bookfair
When: Sun. 10/13
Where: Back Bay
Cost: Free
Info: Enjoy free cozy tea blends as you find your next haunted read at Trident. If you want to get the full experience, you can treat yourself and pay for a birth chart reading or some face painting. Don’t forget to search for your next wicked treasure at the magical trinket market too.
When: Sundays, starting 10/13 - 10/27
Where: Cambridge
Cost: Free
Info: Warm up those vocal chords as you sing your favorite hits. Grab a bevy and a burger and enjoy the show or get up on stage and show your stuff!
73) MFA Open House: Free Admission on Indigenous Peoples’ Day
When: Mon. 10/14
Where: Kenmore
Cost: Free
Info: Head to the MFA and enjoy free admission during Indigenous Peoples’ Day. Explore the new ‘Georgia O’Keeffe and Henry Moore’ exhibit and more during this Open House event.
74) Indigenous Peoples’ Day: Free Admission to the ICA
When: Mon. 10/14
Where: Seaport
Cost: Free
Info: In honor of Indigenous Peoples’ Day, you can go to the ICA for free. Learn about the contemporary art pieces on display, enjoy waterfront and skyline views of the city, and feel inspired.
75) Opening Our Doors Art + Cultural Festival
When: Mon. 10/14
Where: Fenway
Cost: Free
Info: It’s the 23rd annual free Opening Our Doors Festival in Fenway. Explore the Fenway Cultural District for art exhibitions, activities, live music and dance performances. Plus, you can enjoy free admission to the MFA, the Gardner, MAAM, and the Christian Science Publishing House & Mapparium.
76) BFW 2024: Every Body Belongs
When: Tue. 10/15
Where: Brighton
Cost: Free
Info: Head to The Speedway for this all-inclusive event as part of Boston Fashion Week. This fashion show is unique, featuring presentations by different designers and artists as well as theatrical performances with models of all ages, abilities, and sizes.
77) Pour Art/Fluid Acrylics Pop-Up @ The Anchor
When: Tue. 10/15
Where: Charlestown
Cost: Free
Info: Time to express yourself at this pour art class at the Anchor. Enjoy waterfront views, a drink, and good company as you learn how to master the medium of fluid acrylics.
When: Wed. 10/16
Where: Beacon Hill
Cost: Free
Info: Prioritize your mental and physical health and treat yourself at this event! Enjoy free massages and wellness workshops as you relax, shop, and meet some other empowering women in the community.
79) Moon Over Bow
When: Wed. 10/16
Where: Somerville
Cost: Free
Info: Get witchy at this spooky event at Bow. Shop small batch crafts, get a tarot or psychic reading, grab an aura photograph, and so much more at this event where you’ll feel connected to the ~other~ world.
When: Wed. 10/16
Where: Seaport
Cost: Free
Info: Change the vibe of your WFH space by making your way to the Capitol One Cafe where you can enjoy free coffee and meet some other folks around the city. Make sure to RSVP to reserve your spot.
81) Retro Video Game Night at Dorchester Brewing
When: Thu. 10/17
Where: Dorchester
Cost: Free
Info: Enjoy some brews and cocktails as you get down to business and compete with friends – it’s Retro Video Game Night where you can play classic video games that will transport you back in time.
82) 16th Annual Boston Asian American Film Festival
When: Thu. 10/17 - Sun. 10/27
Where: Chinatown
Cost: $5+
Info: Watch films, meet filmmakers, and listen to discussions about the craft of filmmaking as you learn about the Asian American experience through representation on the big screen.
83) Crimson Madness
When: Fri. 10/18
Where: Allston
Cost: Free
Info: Watch a Harvard basketball game for free! There will be music, lawn games, raffles, and more for the entire family to enjoy as you cheer on the Crimson. Get there early for a voucher to Roxy’s Grilled Cheese food truck too.
84) The Head of the Charles Regatta 2024
When: Fri. 10/18 - Sun. 10/20
Where: Charles River
Cost: Free
Info: It’s time for one of Boston’s quintessential celebrations along the Charles. Come watch and cheer on competitors at the Regatta, enjoy stunning views of the water and the color changing trees along the river, and bring a picnic as you feel the energy of the city reach new heights.
85) National Reuse Day Celebration
When: Sat. 10/19
Where: Roxbury
Cost: Free
Info: Come join this community celebration that focuses on reusing things and creating less waste. Bring old clothes and tie dye them; bring broken items and learn how to fix them; enjoy free food; and more!
86) Coding Workshop for Girls @ Northeastern
When: Sat. 10/19
Where: Kenmore
Cost: Free
Info: Have you always wanted to learn to code? Now’s your chance! Stop by at this beginner-friendly workshop where computers and guidance will be provided. Come learn a new skill and meet some friends at this accessible coding lesson.
87) 20s & 30s Halloween Party at Scorpion Bar
When: Sat. 10/19
Where: Seaport
Cost: Free
Info: Enjoy free admission to the Scorpion Bar as you dance the night away in your best costume. Come make friends with new folks in the area at one of the most energetic spaces in Seaport.
88) fruitstand presents: John Queere Dance Pop Party
When: Sat. 10/19
Where: Cambridge
Cost: $10
Info: Come to this dance party hosted by fruitstand, an organization that hosts queer nightlife events. Show off your moves to the greatest hits of Chappell Roan, Charli XCX, Cowboy Carter, and more!
89) Dray’s Non-Alcoholic Beer Garden: Notoberfest
When: Sat. 10/19
Where: Cambridge
Cost: $10
Info: Enjoy the vibes of a classic beer garden without the alc. So stop by the country’s first ever NA beer garden for some NA beer, NA wines, NA cocktails, and some fun activities.
90) Yappy Hour After Brunch at the Urban Grape
When: Sat. 10/19
Where: Cambridge
Cost: $10
Info: Enjoy a wine tasting with your pupper. Come meet new friends (both human and furry alike) and shop from a local maker pop-up too. Plus, there’s guaranteed free treats for your best pal, so everyone is happy!
91) Sweet Halloween at Cider Hill Farm
When: Sat. 10/19 - Sun. 10/20 & Sat. 10/26 - Sun. 10/27
Where: Amesbury
Cost: Free
Info: Head to the beloved Cider Hill Farm for some fun Halloween activities. You’ll need to pay for a ticket if your little one wants to trick-or-treat, or you can stop by, enjoy the vibes, and cheer on everyone’s costumes.
92) Open Streets Boston 2024: Allston/Brighton
When: Sun. 10/20
Where: Allston & Brighton
Cost: Free
Info: Ready to explore the best of Allston & Brighton. It’s time to get up close and personal with ‘Rat City’ at the final Open Streets Boston 2024 of the season. Walk along the car-free street, meet your neighbors, enjoy live performances, and learn about local businesses!
93) SomerStreets: Monster Mash
When: Sun. 10/20
Where: Somerville
Cost: Free
Info: Get dressed in your best costume and come join the big parade on Somerville Ave. Watch an interactive puppet show, cheer on some parkour performers, shop at a craft and vintage market, and listen to live music at this street festival for all ages.
When: Sun. 10/20
Where: Newton
Cost: Free
Info: It’s not fall without the Newton Harvest Fair Festival. Shop locally handmade goods, learn about eco-friendly practices, listen to live music, and watch local performers. Don’t forget to come and decorate your own pumpkin and grab some food from one of the international food trucks.
95) Horror Book Fair with Trident Booksellers
When: Wed. 10/23
Where: Downtown
Cost: Free
Info: Head to Sam Adams for some spooky reads – Trident will be having a pop-up featuring horror to graphic novels as you sip some seasonal brews. There will also be tarot card readings and other fun activities.
96) Game Night
When: Wed. 10/23
Where: Back Bay
Cost: Free
Info: Head to the Goethe-Institut for board and card games. You can practice German or just speak in English as you meet new friends over some casual competition!
97) Fall Festival on The Greenway
When: Thu. 10/24
Where: The Greenway
Cost: Free
Info: Head to The Greenway for the ultimate fall party. Enjoy glow-in-the-dark mini golf, face painting, pumpkin decorating, food trucks and more. Don’t forget to catch ‘Beetlejuice’ at Rowes Wharf to end the night too.
98) ArtsThursdays: Sea Monsters
When: Thu. 10/24
Where: Cambridge
Cost: Free
Info: Head to the Harvard Museums of Science and Culture for a night that will transport you into the depths of the ocean. Come view the new ‘Sea Monsters: Wonders of Nature and Imagination’ exhibit where you can explore the stories behind sea serpents, the kraken and more. Make your own felted sea monster, take part in a community art piece, and meet scientists who will share their work on octopi!
99) Nightmare in the Navy Yard
When: Fri. 10/25
Where: Charlestown
Cost: Free
Info: Head to The Anchor for a waterfront Halloween experience. There will be live music, themed desserts, drink and food specials, a movie lounge, and the city’s largest urban pumpkin patch featuring over 450 traditional and specialty pumpkins!
100) The Guinness Spook of World Records: A Halloween Musical Radio Drama
When: Fri. 10/25
Where: Salem
Cost: $0+
Info: Watch this funky musical about 5 Guinness World Record Holders who didn’t get captured by monsters at the Guinness conference. You’ll have a laugh, and it’s perfect for folks of all ages. Donations encouraged!
101) Boston Book Festival 2024
When: Fri. 10/25 - Sat. 10/26
Where: Back Bay
Cost: Free
Info: One of Boston’s most iconic festivals is back: Boston Book Festival 2024. Come listen to your favorite authors, find your next favorite read, and meet other bookworms at this event that celebrates all-things literature!
102) Hocus Pocus Recreation at Historic Ropes Mansion
When: Fri. 10/25 - Thu. 10/31
Where: Salem
Cost: Free
Info: If you’re a ‘Hocus Pocus’ fan, head to Salem to see this house that is decorated in the ‘90s cult classic fashion. Perfect for photo ops and a walk around the mansion’s historic garden too.
When: Sat. 10/26
Where: Southie
Cost: Free
Info: Come celebrate Halloween early at The LOT. Carve and paint pumpkins, enjoy Halloween-themed games, grab some food and drinks from local food trucks and so much more.
104) 20th Annual Jamaica Plain Canine Costume Parade
When: Sat. 10/26
Where: Jamaica Plain
Cost: Free
Info: This event will put a smile on your face that will last for days. Watch a parade of furry friends dressed in the wackiest and most creative costumes. You can also register your pet if you want to participate too. Charge your phones so you can take plenty of pictures of the best doggos in the city.
105) Rummage Sale
When: Sat. 10/26
Where: West Roxbury
Cost: Free
Info: Donate clothes, linens, and shoes or purchase a $5 bag for a good cause. You’ll be saving the environment and supporting local camperships and scholarships!
106) Fall Fest at the Armenian Church
When: Sat. 10/26
Where: Belmont
Cost: Free
Info: Experience Armenia through cuisine and community connection. Try some kebabs, choreg, and paklava, and learn about Armenian culture!
When: Sat. 10/26
Where: Fenway
Cost: Free
Info: Head to Time Out for the ultimate Halloween party. Come dressed as a good witch or bad witch, enjoy themed-cocktail specials, watch a drag performance, and so much more!
When: Sun. 10/27
Where: Charlestown
Cost: Free
Info: Head to The Anchor for some trick-or-treating fun! Get some candy, sip on some brews, watch a pumpkin carving demo, and soak in waterfront views at this family-friendly event. Costumes encouraged!
109) Harvard Art Museums at Night
When: Thu. 10/31
Where: Cambridge
Cost: Free
Info: Happy Halloween! Come spend it at the Harvard Art Museums where you can explore the galleries, enjoy live DJ tunes, sip on drinks, and munch on light bites.
110) Movie Night: ‘Beetlejuice’
When: Thu. 10/31
Where: Brighton
Cost: Free
Info: Spend Halloween watching a cult classic that completely embodies the spooky spirit. Bring your friends and family for a fun movie night!
111) 11 Places to See Fall Foliage Around Boston
When: Tue. 10/1 - Thu. 10/31
Where: Boston
Cost: Free
Info: Boston turns into the most beautiful place in the fall. Find the best spots to explore the city by foot so you can enjoy the fiery shades of autumn. And if you’re looking for a little getaway, explore New England’s top foliage spots too.
112) 10 Best Neighborhoods in Boston to See Halloween Decorations
When: Tue. 10/1 - Thu. 10/31
Where: Boston
Cost: Free
Info: Get in the festive Halloween spirit by exploring Boston neighborhoods and seeing fun decorations around the city. It’s the perfect way to get lost along the red-bricked alleyways and homey apartments and marvel at your neighbors’ spooky creativity!
113) 20 Trivia Nights in Boston for Every Day of the Week
When: Tue. 10/1 - Thu. 10/31
Where: Boston
Cost: Free
Info: Put your knowledge to the test every day of the week if you wish! Explore fun trivia nights all around the city with your friends as you grab a bite to eat and drink too.
114) 10 Free Wine Tastings In and Around Boston
When: Tue. 10/1 - Thu. 10/31
Where: Boston
Cost: Free
Info: Learn about wine in friendly environments all over the city. Whether you are new to the wine world or a connoisseur, come learn about new blends and vinos with folks in the community.
115) Boston’s Best Places to Work Remotely that Aren’t a Coffee Shop
When: Tue. 10/1 - Thu. 10/31
Where: Boston
Cost: Free
Info: As the weather gets a bit cooler, it’s time to find your next cozy hideaway while you work remotely. There’s plenty of places around the city for a nice change of scenery. Don’t forget to check out Shy Bird on the first Friday of every month for complimentary lunch with a remote work reservation!
BONUS: These things are worth the price!
When: Tue. 10/1 - Thu. 10/31
Where: Seaport
Cost: $25+
Info: Get ready to immerse yourself in spooky worlds with four ghoulish experiences that are perfect for haunted vibes at night. Don’t worry, though, since anyone can enjoy! Families and adults who aren’t fear fans are welcome to enjoy the multiple beer gardens, great food, and interactive props.
When: Fri. 10/4
Where: Seaport
Cost: $30
Info: Put on your grungiest outfit that embodies your punk, rock and roll, metal spirit and head to the ICA for gorgeous waterfront views and even more beautiful contemporary art. Get ready to eat, drink, and dance to live music too.
Friday Night Yoga & Live Music at the Museum of Modern Renaissance
When: Fri. 10/4
Where: Somerville
Cost: $35
Info: Reset and recharge at one of the most beautiful and underrated museums in Boston. As you enjoy a community yoga practice, you’ll also be able to listen to calming live piano music as your mind gets lost in the stunning intricacies of the building.
When: Thu. 10/10
Where: Kendall
Cost: $15
Info: It’s an adults-only kind of night that combines the best of art and science! Sip on some drinks and munch on some snacks as you engage in immersive demos, tastings, and conversations.
When: Wed. 10/16
Where: Downtown
Cost: $60
Info: Head to the Boston Public Market to celebrate the local food scene with a carnival twist! As you taste the best from Boston’s best chefs, you’ll also be able to play carnival games, participate in a live action, and take photos with GIANT pumpkins.
When: Fri. 10/25
Where: Fenway
Cost: $15-25
Info: MFA Late Nites are back for an after-hours party. Explore the many galleries, dance to live music, make some art, sip on some bevs, and munch on some great food as you experience the MFA in a new light.
Something Strange: An ‘80s Halloween
When: Sat. 10/26
Where: Seaport
Cost: $40
Info: The ultimate Halloween bash is happening at the ICA. Wear your best ‘80s costume and show your grooviest moves on the dance floor while enjoying art, groovy tunes, drinks, food, and pop-up performances.
21 Best Farms to PYO Apples, Pumpkins, and Other Produce
When: Tue. 10/1 - Thu. 10/31
Where: Surrounding Areas
Cost: Pay as you go
Info: Come explore local farms around Boston and their wide variety of produce and goods. Some have free entry, so you can pay as you go when you PYO apples, pumpkins, and other fruits, veggies, and flowers. This is the ultimate fall activity!
11 Best Pumpkin Patches Near Boston
When: Tue. 10/1 - Thu. 10/31
Where: Surrounding Areas
Cost: Pay as you go
Info: Ready to find the perfect and plumpest pumpkin of them all? Go on an adventure and hunt for the best gourd for carving, painting, and decorating!
When: Tue. 10/1 - Thu. 10/31
Where: Surrounding Areas
Cost: $8+
Info: Grab your friends and put your communication skills to the test as you navigate your way through the most fun, windy, and creative corn mazes around Boston!
19 Best “Happy Hour” Food & Drink Deals that are Actually Worth It
When: Tue. 10/1 - Thu. 10/31
Where: Surrounding Areas
Cost: Pay as you go
Info: Enjoy the best food and drink deals around the city! There’s plenty of cuisine to discover around Boston from maki and steak frites to tapas and oysters.
