Boston events September 2019. Things to do in Boston.

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Best events for 12 months

Boston events September 2019

Country fair

September 1, 2019
(begins Aug. 30)
64 miles west
The Spencer Fair is a traditional country fair with horse and tractor pulls, farm exhibits, farm animals (cattle, chickens, rabbits), giant pumpkins, a carnival midway, live music, and a demolition derby at Spencer Fairgrounds.

Campfire music festival

September 1 - 2, 2019
(begins Aug. 30)
3.6 miles NW
Hear new performers and watch songwriters interact and swap tunes as they sing in the round Labor Day weekend at Campfire Festival at Club Passim. Repeats in May.

Sailing festival

September 1 - 2, 2019
(begins Aug. 30)
35 miles NE
Gloucester Schooner Festival has a block party Friday evening. Saturday includes a lobster bake, a concert, a boat parade of lights, and fireworks. The Parade of Sail is Sunday morning before the Mayor’s Race.

Medieval fair

September 1 - Oct. 20, 2019
(begins Aug. 31)
49 miles south
King Richard’s Faire offers medieval food, games, and artisan shops, plus costumed acrobats, battling knights, fire-eaters, jugglers, dancers, and puppeteers in a forest near Carver. Open weekends plus Sept. 2 and Oct. 14 in 2019.

Labor Day festival

September 2, 2019
28 miles north
The Bread & Roses Heritage Festival presents music, theater, dance, and puppets on three stages, and it has vendors of food, arts & crafts, and merchandise in downtown Lawrence. Free.

Scrapbook Expo

September 6 - 7, 2019
37 miles west
Scrapbookers will find classes, vendors, and crop parties at the Stamp & Scrapbook Expo at Best Western Royal Plaza Hotel in Marlborough.

Arts festival

September 7 - 8, 2019
0.3 miles east
The Boston Arts Festival features 70 local visual artists and craft makers, plus musicians performing onstage at Christopher Columbus Waterfront Park. Free.

Oktoberfest

September 7 - 8, 2019
25 miles SW
Celebrate Oktoberfest with live music and dancing, kids’ games, German food, beer, wine, and crafts in a covered pavilion at the German club in Walpole.

Halloween on the farm

September 7 - Nov. 3, 2019
22 miles north
A ticket to Connors Farm Corn Maze also includes hayrides, pedal carts, and activities in Danvers. The flashlight maze and haunted farm are only open Friday and Saturday nights, plus a few extra days.

Small-town blues festival

September 8, 2019
(12 to 6 p.m.)
41 miles south
Bring a lawn chair to the $20 New England Blues Festival [website has sound on some devices] at Middleboro Lodge of Elks to support charity. Food and beverage vendors.

Beer at the zoo

September 14, 2019
(5 to 7:30 p.m.)
8.2 miles north
Taste beer from 20 breweries with food samples, and stroll among animal exhibits during Ales & Tails at Stone Zoo for age 21+.

Food festival

September 15, 2019
0.4 miles NW
Boston Local Food Festival serves locally grown and sustainably produced food, local music, chef demos, educational exhibits, vendors, and a family zone at Rose Kennedy Greenway. Free.

Gourmet wine & food festival

September 19 - 22, 2019
74 miles south
Taste wine on the lawn of Marble House, attend seminars and celebrity chef demonstrations, and enjoy wine dinners during Newport Mansions Wine & Food Festival in Newport, RI for age 21+.

Cannabis rally

September 20 - 22, 2019
1 mile SW
Boston Freedom Rally celebrates legal marijuana in Massachusetts with inspirational speakers, two stages of live music, and vendors at Boston Common. Free.

Street food

September 21, 2019
2.5 miles SW
A ticket to Phantom Gourmet Food Festival gets you samples of 100 kinds of food, with beverages for sale near Fenway Park. Must be age 21+. Expect lines.

Beer festival

September 21, 2019
46.6 miles west
Mass Fermentational [formerly Mass Brewers Fest] offers unlimited samples from 50 breweries plus food trucks outdoors in Worcester Common. No pets.

Beer festival

September 21, 2019
67 miles SE
Sample 250 beers from 75 breweries at Cape Cod Brew Fest at the Cape Cod Fairgrounds in East Falmouth for age 21+.

Visit art studios

September 21 - 22, 2019
1.6 miles SW
Follow the map to visit studios of 200 local artists plus local galleries during South End Open Studios. Free.

Welcome autumn

September 22, 2019
3.5 miles west
Say goodbye to summer and celebrate the first day of fall with a folk band, a puppet parade from Harvard Square to the Charles River, and a sing along at Revels RiverSing. Free.

Marshmallow festival

September 28, 2019
2.8 miles NW
What the Fluff? celebrates marshmallow cream with games (Sticky Musical Chairs and Fluff Jousting), cooking and eating competitions, a kids’ area, and live music at Union Square in Somerville, where Fluff was invented in 1917. Postponed if it rains. Free.

Food festival

September 28, 2019
3.5 miles NW
Let’s Talk About Food has cooking demonstrations, food talks and panels, samples, local chefs, and nutritionists in Cambridge.

Blacksmith festival

September 28, 2019
47 miles NW
Fitchburg Forge-in celebrates the art of blacksmithing with competitions, demonstrations, family art activities, music, arts and crafts, and food vendors at Riverfront Park in Fitchburg.

Home show

September 28 - 29, 2019
16 miles north
See home improvement products, services, and demos at Suburban Boston Fall Home Show at Shriners Auditorium in Wilmington. Repeats in Jan.

Comedy festival

September 2019
(undated)
Boston locations
Boston Comedy Festival stars 96 innovative comedians from around the world competing for prizes.

Fashion week

September 2019
(undated)
Boston locations
Boston Fashion Week showcases the work of local fashion designers with runway shows, exhibits, panels, receptions, and networking parties.

Film festival

September 2019
(undated)
multiple locations
Boston Film Festival (BFF) is dedicated to supporting evolving filmmakers by screening their new films. Directors attend Q & A sessions after some films.

Free museum day

September 2019
(undated)
Statewide
Get a free ticket that allows two people to visit one of the many museums participating in Museum Day Live.

Young achievers conference

September 2019
(undated)
multiple locations
Under 30 Summit is a pricey series of music, food, drink, networking, famous speaker, and public service events for young entrepreneurs and game-changers.

Bicycle ride

September 2019
(undated)
0.1 miles west
Ride through historic neighborhoods and see views of the Charles River from car-free Storrow Drive (plus Boston Harbor on the longer route) during the Hub on Wheels bike ride, with a choice of 12 or 40 miles.

Boston Night Market

September 2019
(undated)
0.1 miles west
Shop for food and merchandise, visit the beer garden, and play games at the Boston Night Market in City Hall Plaza. Children age six and younger are free.

Free fitness festival

September 2019
(undated)
0.1 miles west
Boston Social Fitness Festival promises “fun activities for all ages and fitness levels” at Boston City Hall Plaza. Free.

Free country music

September 2019
(undated)
0.2 miles west
This year’s Country in the City Concert features Granger Smith on City Hall Plaza. Free.

Asian festival

September 2019
(undated)
0.7 miles SW
Asian American Day Gala offers performances, food, music, art activities, and a business showcase at Boston Common. Free, registration is not required.

Chinatown festival

September 2019
(undated)
0.9 miles south
Experience Chinatownpromises music and dance performances, family-friendly workshops, and pop-up events at three locations in Boston Chinatown. Free.

Oktoberfest - Boston

September 2019
(undated)
1.5 miles SE
Harpoon Octoberfest features beer, bratwurst, waltzing musicians in lederhosen, and contests in tents at Harpoon Brewery for age 21+.

Outdoor concert

September 2019
(undated)
1.5 miles SE
MixFest is a popular concert with an all-star line-up of artists at Blue Hills Bank Pavilion. Free.

Run on Spectacle Island

September 2019
(undated)
Seaport is 1.5 miles SE
The Island Run is a 5K or 5-mile run on the trails of Spectacle Island, followed by a lunch and awards as you cruise back through Boston Harbor.

Cambridge carnival

September 2019
(undated)
1.8 miles west
Cambridge Carnival features a 12:30 p.m. parade of revelers in colorful handmade costumes dancing to a steel band, a stage for world music and local bands, a kids’ fest, international foods, and craft vendors. Free.

Jazzy block party

September 2019
(undated)
2 miles SW
Family friendly Berklee Beantown Jazz Festival offers three stages of live music, arts, crafts, food, and even an instrument petting zoo on Columbus Avenue (from Massachusetts Avenue to Burke Street). Free.

Street festival

September 2019
(undated)
2.2 miles SE
South Boston Street Festival features live music and dance on two stages, 100 artists and local merchants, fair food, and children’s activities on East Broadway (from I to L Street). Free.

Buy American

September 2019
(undated)
2.4 miles SE
Shop from vendors selling American-made goods at the American Field market at The Innovation and Design Building in the Seaport neighborhood. Free.

College student festival

September 2019
(undated)
2.5 miles SW
CollegeFest is a back-to-school event with live music, student entertainment, prizes, and giveaways at Fenway Park. Free.

Improvised comedy festival

September 2019
(undated)
3 miles west
Boston Improv Festival [formerly Boston Comedy Arts Festival] promises “a carefully curated selection of experienced, inspiring acts from around the country and beyond” to keep you laughing at ImprovBoston.

Street festival

September 2019
(undated)
4.1 miles west
Allston Village Street Fair offers activities for families, two stages of live bands, street performers, an artist and vendor market, international food, and an amusement area on Harvard Avenue (from Cambridge St. to Brighton Ave.) in Allston. Free.

Jamaica Plain music festival

September 2019
(undated)
4.6 miles SW
JP Music Festival has two stages of music by 20 local artists and bands, plus food trucks and children’s activities northeast of Jamaica Pond. Free.

Beer tasting at the library

September 2019
(undated)
6 miles north
Taste local craft beer, cider, and restaurant food at Brews for Books, with live music and games in the historic art galleries at Malden Public Library.

Greek festival

September 2019
(undated)
6.5 miles SW
Taste Greek food and pastries, dance to live music, and watch folk dancing at the GreekFest Boston in Brookline. Free.

Taste of Winthrop

September 2019
(undated)
6.7 miles NE
Taste food from local restaurants, caterers, cafes, and bakeries at Taste of Winthrop, with views and entertainment at the Winthrop Yacht Club.

Grilled cheese festival

September 2019
(undated)
9.1 miles west
A $10 ticket (child $8) includes all-you-can-eat grilled cheese sandwiches and outdoor activities at The Great Grilled Cheese Festival at the American Legion in Newton.

Music on a farm

September 2019
(undated)
16.1 miles south
Festival at the Farm offers live music on two stages, local food & drink, backyard games, a kids’ zone, and an on-site farmers’ market at Prowse Farm in Canton.

Country music festival

September 2019
(undated)
30.7 miles SE
South Shore Country Festival is an all-ages event with food vendors and 10 bands in Marshfield.

Irish festival

September 2019
(undated)
31 miles SW
South Shore Irish Festival features Irish and Irish-American performers onstage, plus family entertainment and vendors in Marshfield. Children 12 and younger are free.

BBQ on the mountain

September 2019
(undated)
50 miles west
The BBQFest features roasted pig, oysters, chili, pulled pork, live music, a beer tent, craft vendors, and a farmer’s market at Wachusett Mountain.

Reggae festival in Providence

September 2019
(undated)
52 miles SW
Hear bands, shop for crafts, and buy Jamaican food, beer, and cocktails at Waterfront Reggae Festival at Bold Point Park in East Providence, RI.

Newburyport music festival

September 2019
(undated)
37 miles NE
Bring a blanket or chair to Newburyport’s Riverfront Music Festival, which has music, food vendors, and a beer garden at Waterfront Park in Newburyport. Free.

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