55 Fall Festivals around Boston in 2025
When:
Friday, Sep 12, 2025 12:00p -
Sunday, Nov 16, 2025 8:00p
Friday, Sep 12, 2025 12:00p -
Sunday, Nov 16, 2025 8:00p
Where:
Boston
Surrounding areas
Boston, MA
Admission:
$Varies
Categories:
Art, Date Idea, Drinks, Festivals & Fairs, Food, Games, Good for Groups, History, Innovation, Kid Friendly, Music, Party, Pet Friendly, Seasonal, Shows, Social Good
Event website:
https://www.thebostoncalendar.com/
Fall is fast approaching! As the sweaters come out and the pumpkin spice lattes waft across the Boston Common, put a few of these fall festivals into your calendar. From dynamic film festivals to classic New England farm festivals, these events will help you settle comfortably into the cozy season.
by Celina Colby & Yelena Nicolle Salvador
Events are listed chronologically.
When: Sat. 9/13
Where: Somerville
Cost: Free
Info: Watch an extensive lineup of live local music, engage in free children’s activities for the whole family, shop at a vendor marketplace run by the Boston Women’s Market, and enjoy a spectacular fireworks show.
2) G'25: Gilman Square Arts & Music Fest
When: Sat. 9/13
Where: Somerville
Cost: Free
Info: Have fun at this annual block party featuring an arisan market, food vendors, live bands, a wandering circus, and other fun activities for friends and family.
3) KickBack Boston Presents: One Day Only Fest 2025
When: Sat. 9/13
Where: Downtown
Cost: Free
Info: Live, local DJs will be the baseline for this joyful festival celebrating emerging artists and BIPOC joy. Food and drinks (alcoholic and nonalcoholic) will also be available for purchase.
When: Sat. 9/13
Where: Revere
Cost: Free
Info: Watch artmaking in real time at the Revere Beach Arts Fest where a live art competition is just the start of the excitement. Create your own works and enjoy music, food, and the beautiful beach scenery during the festival.
5) Caribbean Rum & Food Festival
When: Sat. 9/13
Where: Roxbury
Cost: $35+
Info: Celebrate the flavors and sounds of the Caribbean at this festival showcasing food and cocktails from the tropical region. The culinary offerings will be accented with live entertainment and work by local artists and craftspeople.
When: Sat. 9/13
Where: Watertown
Cost: Free
Info: Jam out to live entertainment, vote for the best chili during the Roche Bros. Cook-Off, bring the family to the Kids Zone, and enjoy more activations at this Watertown festival.
When: Sat. 9/13
Where: Roslindale
Cost: Free
Info: Enjoy a free, neighborhood-wide music festival where you can watch musicians in a huge variety of genres perform on porches, lawns, and parks across Roslindale.
When: Sat. 9/13
Where: Brighton
Cost: Free
Info: Head to the Charles River Speedway for Oktoberfest fun at Notch. Participate in stein-holding, pretzel-eating, and lederhosen-wearing competitions while sipping on great brews and listening to live music.
9) Fens Fest at the Fenway Victory Gardens
When: Sat. 9/13
Where: Fenway
Cost: Free
Info: Spend an early fall afternoon in the Fenway Victory Gardens enjoying live music, food from neighborhood vendors, and the still-in-bloom gardens before the first frost arrives.
When: Sat. 9/13 - Sun. 9/14
Where: Union Square
Cost: Free
Info: Celebrate the start of Oktoberfest season at Bow Market with stein-holding competitions, a Lederhosen Lager Run, live music, and other family-friendly activities.
11) Dorchester Brewing Oktoberfest
When: Sat. 9/13 & Sat. 9/27
Where: Dorchester
Cost: Free
Info: You don't have to travel far to feel like you're in Germany. Get ready for two weekends full of German fare at Dorchester Brewing. There will be free sour apple cotton candy, German music, German food, and German beers.
12) Boston Local Food Festival
When: Sun. 9/14
Where: Greenway
Cost: Free
Info: You certainly won’t go hungry at this festival! The celebration features nearly 100 local food vendors, showcasing some of the best eats Boston has to offer. Sample different dishes while you stroll along the Greenway enjoying the city’s beautiful scenery.
13) Thai Market Fair
When: Sun. 9/14
Where: Harvard Square
Cost: Free
Info: Stop by the first-ever Thai Market Fair in Harvard Square. Experience Thai culture by trying their cuisine, catching traditional performances, shopping from Thai vendors, and more.
14) Open Streets 2025: Dorchester
When: Sun. 9/14
Where: Dorchester
Cost: Free
Info: Explore Dorchester and connect with neighbors at this block party. As you stroll along a car-free street at the heart of Dot, you can listen to live music, shop from local businesses, learn about community partners, and more.
When: Sun. 9/14 & Sun. 21
Where: Back Bay
Cost: Free
Info: Catch the final car-free days on Newbury Street of the 2025 season. Connect with local businesses, grab a bite to eat, listen to live music, and enjoy this block party before it gets too cold.
When: Wed. 9/17
Where: City Hall Plaza
Cost: Free
Info: The weather is still perfect for some outdoor fitness classes. Relax and meet new friends while enjoying complimentary yoga classes of various levels. Grab a bite to eat from a food truck, listen to some speakers, and grab an ice cream sundae.
17) Greek Festival at Annunciation Greek Orthodox Cathedral
When: Fri. 9/19 - Sun. 9/21
Where: Brookline
Cost: Free
Info: There’s a Greek festival coming to Brookline. Savor Greek cuisine, watch traditional performances, and search for a treasure at antique vendors.
18) Sam Adams Oktoberfest Weekend
When: Fri. 9/19 - Sun. 9/21
Where: Jamaica Plain & Downtown
Cost: $10+
Info: Experience Bavaria at Sam Adams locations across Boston. All weekend long, you can enjoy live music, stein-holding competitions, food pop-ups, and specialty brewery tours.
19) 41st Annual Boston Film Festival
When: Fri. 9/19 - Mon. 9/22
Where: Boston
Cost: $0+
Info: Check out one of America's longest-running film festivals. Grab tickets to different showings (some are even complimentary) and explore stories from across genres: short films, international films, animation, sports, and more.
20) Taiwan Film Festival of Boston
When: Fri. 9/19 - Sun. 10/12
Where: Boston
Cost: $20+
Info: The Taiwan Film Festival of Boston will showcase short and feature-length films around different spaces in the city. Catch screenings at the MFA, AMC Causeway, and other locations.
When: Sat. 9/20
Where: South Boston
Cost: Free
Info: Every year, more than 5,000 guests come to revel at the South Boston Street Fest, a mammoth festival featuring two entertainment stages, food, drinks, children’s activities, and a huge market of local vendors. Come celebrate its 25th anniversary!
When: Sat. 9/20
Where: Brighton
Cost: Free
Info: Come celebrate the beginning of fall with a cowboy twist. Head to Boston Landing for some Western fun with line dancing lessons, a reptile show, live music, country BBQ, and more.
23) Boston Rodeo & Country Music Festival
When: Sat. 9/20
Where: City Hall Plaza
Cost: $61.48+
Info: Yeehaw your way to City Hall Plaza since the rodeo is coming to town. Watch a pro rodeo show, learn how to line dance, ride a mechanical bull, listen to country music, and cheer on the barrel racers.
When: Sat. 9/20 - Sun. 9/21
Where: Somerville
Cost: $10
Info: Make your way to Aeronaut to celebrate beer season. Listen to a live polka band, sip on German-inspired beers, and munch on snacks like schnitzel sandos, braised brats, and more.
25) What the Fluff? Festival 2025
When: Sat. 9/21
Where: Somerville
Cost: Free
Info: In celebration of the invention of fluff in Somerville, the What the Fluff? Festival offers fluff games, fluff competitions, and more fluff recipes for sampling than you ever thought possible.
26) Cambridge Science Carnival
When: Sun. 9/21
Where: Cambridge
Cost: Free
Info: This festival celebrates Science, Technology, Engineering, Art, and Math (STEAM) with a series of fun and interactive activities, demonstrations, workshops, and performances.
When: Wed. 9/24
Where: Fenway
Cost: $50
Info: Celebrate the culinary scene of the Fenway neighborhood at this festival. With your ticket, you'll get to enjoy unlimited food and drink tastings from over 20 Fenway restaurants.
28) Roslindale Greek Food Festival
When: Fri. 9/26 - Sun. 9/28
Where: Roslindale
Cost: Free
Info: Get in touch with Greek culture at this three-day festival featuring authentic Greek cuisine, wine, and pastries, plus a shopping market of cultural goods.
29) Oktoberfest at Lamplighter Taproom
When: Fri. 9/26 - Sun. 9/28
Where: Cambridge Crossing
Cost: $10
Info: Happy Oktoberfest! Come celebrate at the Lamplighter taproom where there will be cask pours, stein-holding competitions, free beers for those who are best dressed in their lederhosen, and other fun activities.
30) 13th Annual Ignite! Global Street Food and Fire Festival
When: Sat. 9/27
Where: Somerville
Cost: Free
Info: Sample global street food from a wide array of local restaurants, watch unique cultural performances by area artists, and enjoy vivid light (and fire) installations at this annual festival.
When: Sat. 9/27
Where: Roslindale
Cost: Free
Info: Celebrate this beloved food by sampling dumplings from local restaurants and food trucks. Try to pick a favorite, a tough choice between traditional classics and avant-garde innovations, and enjoy live entertainment as you eat throughout the afternoon.
32) Fall Fest at High Street Place
When: Sat. 9/27
Where: Downtown
Cost: Free
Info: High Street Place food hall is throwing their annual autumn bash. Sip on brews at the outdoor beer garden, listen to live music, play some lawn games, make some crafts, and more.
When: Sat. 9/27
Where: Medford
Cost: Free
Info: In a scenic spot along the Mystic River in Medford, watch live music performances, browse works by local artists, eat food, play games, and engage in activities for the whole family.
34) MassRobotics 8th Annual Robot Block Party
When: Sat. 9/27
Where: Seaport
Cost: Free
Info: Join companies, universities, and start-ups as they come together to show off their latest robotic technology in the Seaport. Watch robotic demonstrations, play games, and interact with the robots in a hands-on environment.
35) Oktoberfest Beer Fest Party
When: Sat. 9/27
Where: Fenway
Cost: Free
Info: Time Out Market is hosting the ultimate Oktoberfest party. Sample brews from New England breweries, dine on Oktoberfest-inspired dishes, participate in stein-holding competitions, and more.
36) The Great Northeast Jug Band Festival
When: Sat. 9/27
Where: Arlington
Cost: Free
Info: Celebrating “good time” music from the 1920s and ‘30s through the present day, The Great Northeast Jug Band Festival will have danceable live music outdoors all day long. You can participate in an open jug jam and visit the makers' tent too.
37) Oktoberfest at Long Live Roxbury
When: Sat. 9/27
Where: Roxbury
Cost: Free
Info: Enjoy this free admission Oktoberfest celebration where you can listen to a live brass band, participate in stein-holding competitions, enjoy food pop-ups, shop from a vendor market, and more.
When: Sun. 9/28
Where: East Cambridge
Cost: $0+
Info: Local pitmasters face off at this festival for the title of best ribs in town. Enjoy piled high plates of barbecue, live music, games, and more. Bring your best Gordon Ramsey face to judge between dishes.
39) Fall Festival on the Greenway
When: Fri. 10/3
Where: Greenway
Cost: Free
Info: Celebrate the fall season on the Greenway. Play some glow mini golf, grab a snack from a food truck, decorate a pumpkin, and shop from an artisan market at this mini fest by the waterfront.
When: Sat. 10/4
Where: Dorchester
Cost: Free
Info: This festival and night market celebrate the Mid-Autumn Moon Festival with a spectrum of live entertainment, tons of local food vendors, and engaging family-friendly activities including food contests, lantern-making, and much more.
When: Sat. 10/4
Where: Jamaica Plain
Cost: Free
Info: Head to the Arnold Arboretum for a cross-cultural celebration of art. At this family-friendly festival, you'll get to experience the creativity of Boston's communities of color through spoken word, dance, visual arts, and more.
When: Sat. 10/4
Where: Fenway
Cost: Free
Info: College students with a valid student ID are welcomed to Boston with the ultimate moving-in experience: a free festival in Fenway Park. Listen to live music and collect swag from beloved brands while you meet other local students.
43) Fall Fest at Kendall/MIT Open Space
When: Sat, 10/4
Where: Kendall Square
Cost: Free
Info: On a rooftop in Kendall Square, celebrate the fall season with food, drinks, lawn games, live music, and family-friendly fun for all.
44) HONK! Festival
When: Fri. 10/9 - Sun. 10/12
Where: Somerville
Cost: Free
Info: The HONK! Festival of Activist Street Bands in Somerville is a raucous weekend of music, performances, and over-the-top spectacle. Listen to music, participate in art-making, march in the parade, and stand up for social justice all in one place.
When: Sat. 10/11
Where: Assembly Row
Cost: Free
Info: Meet new friends and celebrate fall at Club Volo Oktoberfest. Play pickleball, lawn games, and volleyball; grab a drink from the on-site bar, participate in stein-holding competitions; and more.
46) 46th Annual Harvard Square Oktoberfest
When: Sun. 10/12
Where: Harvard Square
Cost: Free
Info: Celebrate Oktoberfest at this raucous all-weekend festival in Harvard Square. Listen to live music on multiple stages, sample food from international food vendors, experience arts and crafts, and toast at festive beer gardens around the square.
47) Boston Public Market Harvest Party
When: Thu. 10/16
Where: North End
Cost: $50+
Info: Boston Public Market’s annual Harvest Party is not to be missed. Celebrate its 10-year anniversary with bites from the food vendors around the market, live music, dancing, raffles, and more. Don't forget to take pictures with the giant pumpkins and connect with the community.
48) The Head of the Charles Regatta 2025
When: Thu. 10/16 - Sun. 10/19
Where: Charles River
Cost: Free
Info: Watch thousands of rowers from around the globe compete in this stunning water sports competition. In addition to watching the race, you can enjoy food and beverages in The Reunion Village.
49) SpicetoberFest: Spice. Culture. Food
When: Sat. 10/18
Where: City Hall Plaza
Cost: Free
Info: Check out the first-ever Spictoberfest festival which will bring together local flavors and culture to the heart of Boston. Shop from over 40 vendors, farmers, and exhibitors. Check out the Spice Lane featuring hot peppers and hot sauces. Catch a comedy show, chef demos, and so much more.
50) Open Streets 2025: Mattapan
When: Sun. 10/18
Where: Mattapan
Cost: Free
Info: Learn about the Mattapan neighborhood while listening to live music, shopping from local businesses, learning about community partners, and playing lawn games on car-free streets during this afternoon block party.
When: Sat. 10/18 - Sun. 10/19
Where: Roxbury
Cost: Free
Info: Embrace a plant-based lifestyle, or just learn about one, at this comprehensive festival. Sample foods, listen to chef and lifestyle speakers, and shop a marketplace of products geared towards a more sustainable food industry.
When: Sun. 10/19
Where: Newton
Cost: Free
Info: Watch live entertainment from local performers on two separate stages, decorate a pumpkin, shop from the artisan market, and explore international cuisine from food trucks on-site. Kids can enjoy the thrills of the caterpillar rollercoaster as well.
When: Sat. 10/25
Where: Back Bay
Cost: Free
Info: Celebrate the power of words at this all-day festival featuring lectures, workshops, author talks, live music, food trucks, and many other events centered on books and reading. There’s no better time to find your next read or work up the courage to ask for an autograph from your favorite author.
54) Open Streets 2025: Jamaica Plain
When: Sun. 11/2
Where: Jamaica Plain
Cost: Free
Info: Enjoy the final Open Streets 2025 of Boston in the heart of the beloved JP neighborhood. Take a car-free stroll, listen to live music, shop from local vendors, and so much more at this final block party of the season.
55) Boston Jewish Film Festival
When: Wed. 11/5 - Sun. 11/16
Where: Around Boston
Cost: $15+
Info: The Boston Jewish Film Festival is the largest film-based organization in New England, welcoming 15,000 guests annually to view films by Jewish filmmakers and about Jewish life. Watch screenings around the city and participate in associated events during the festival.
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