Gloucester Waterfront Festival - Glouceser, MA - Aug 17 to Aug 18, 2019
Arts and crafts show with over 200 juried artisans, food vendors, authors and musicians from across the US bring a variety of arts and crafts (across all media) and literature. Includes family style entertainment including live music and performance arts. Free admission, goes on rain or shine, friendly leashed pets welcome.
Oktoberfest at Olde Magoun’s Saloon - Somerville, MA - Sep 4 to Sep 28, 2019
A month of Oktoberfest specials leading up to an all-day Oktoberfest starting with the Bayern Munich match at 9:30am, German food served from noon, ceremonial keg tapping of Paulaner Weisn tapped at 12:30, and music from noon to 8.
South Shore Irish Festival - Marshfield, MA - Sep 7 to Sep 8, 2019
Enjoy live entertainment on multiple stages, corn hole tournament, tug of war competion, Irish magic show, Irish storytelling and more
Swampscott Arts & Craft Festival - Swampsott, MA - Sep 7 to Sep 8, 2019
Annual arts & crafts show – free admission! Goes on rain or shine. Friendly leashed pets welcome.
Somerville Dog Festival - Somerville, MA - Sep 8 to Sep 8, 2019
Annual event with dog sports demonstrations, silent auction, vendors and other activities for the whole family (including your pup!). Free admission but donations are appreciated.
TD Bank Hub on Wheels - Boston, MA - Sep 15 to Sep 15, 2019
Boston’s annual bicycling ride. There are two routes, including a short downtown route, and both of which start and finish on City Hall Plaza. A portion of registration fees benefit Boston Children’s Hospital.
Trails and Sails - Essex County, MA - Sep 20 to Sep 29, 2019
Two weekends of walks and water await you throughout Essex County, with over 150 free events at cultural, historic, and natural sites where you can walk, hike, sail, tour, and embark on other adventures
Fluff Festival - Somerville, MA - Sep 21 to Sep 21, 2019
Fluff, the marshmallow confectionary in a jar, was invented in 1917 in Union Square. This festival celebrates that invention with over 15,000 people, and features musical performances, a cooking contest, Fluff-themed games and activites, and of course, treats made with Fluff!
Boxford Apple Festival - Boxford, MA - Sep 21 to Sep 21, 2019
Held annually on the third Saturday in September by the Boxford Historical Society. Enjoy crafters, tours of a 1760 Holyoke-French House, food including apple favorites, and music
Oktoberfest at DBco - Dorchester, MA - Sep 21 to Sep 21, 2019
Kick off Oktoberfest with fresh Oktoberfest beers in traditional German liter steins, traditional food, live German band and more!
Boston Latino International Film Festival - Boston, MA - Sep 25 to Sep 29, 2019
Annual event featuring films made by Latinos, about various themes and in different genres
Grotonfest - Gronton, MA - Sep 28 to Sep 28, 2019
Enjoy food, arts & crafts, and displays from local businesses and non-profits at Legion Common. Since 1979.
Allston Village Street Fair - Boston, MA - Sep 29 to Sep 29, 2019
A family friendly event celebrating the rich diversity of neighborhood residents, with two outdoor stages, live bands, street performances, international food court, artists and an amusements area. Free parking and free shuttle bus service from the Guest Street Parking Garage.
HUBweek - Boston, MA - Oct 1 to Oct 3, 2019
Topsfield Fair - Topsville, MA - Oct 4 to Oct 14, 2019
Held annually since the first cattle show in 1820. Giant pumpkin weigh-off, Essex County pageant, sheep show, goat show, racing pigs, farmyard, petting zoo, kiddie korral and more.
Textile River Regatta - Lowell, MA - Oct 6 to Oct 6, 2019
39th annual event on the Merrimack River.
The Taste of WGBH Food Wine Festival - Boston, MA - Oct 10 to Oct 13, 2019
A three day festival with events and activities across the city, featuring the best culinary talents of the area, including Chef’s Gala, wine and craft beer paired dinners, tasting event and Food Fight chef competition. Educational seminars, live music, and more! All-inclusive tickets get you into all events for one price, plus a wine glass to use for sampling.
Honk! Festival - Somerville, MA - Oct 11 to Oct 13, 2019
A festival of activist street bands. You’ll hear honking horns, beating drums and see flags waved by people of all ages, classes, ethnicities and backgrounds.
Head of the Charles Regatta - Boston, MA - Oct 19 to Oct 20, 2019
Hundreds of thousands come to the banks of the Charles River to row or watch the Regatta since it was started in 1965.
Boston Vegetarian Food Festival - Boston, MA - Oct 19 to Oct 20, 2019
Hosted by the Boston Vegetarian Society and held at Reggie Lewis Athletic Center with free admission, free food sampling, free speaker presentations, free parking, kids activities and more.
Essex Clamfest - Essex, MA - Oct 26 to Oct 26, 2019
Food and fun with lots of vendors. The highlight is the annual Clam Chowder Tasting competition in Memorial Park.
Boston Christmas Festival - Boston, MA - Nov 8 to Nov 10, 2019
32nd annual. Shop from 300 craft vendors just in time for the holidays. Admission is $15 with kids under 14 free. Held at the Seaport World Trace Center.
Boston Comedy Arts Festival - Cambridge, MA - Nov 13 to Nov 16, 2019
Lots of entertainment and workshops at this annual event. Over 300 artists perform in a wide variety of musical and comedy acts. Features sketch, standup, and improv comedy for 5 days of non-stop fun. Held at ImprovBoston near Central Square T station.
Boston Comedy Festival - Somerville, MA - Nov 13 to Nov 16, 2019
This four day festival features hundreds of comedians from around the world for comedy shows, workshops, and special events.
Paradise City Marlborough - Marlborough, MA - Nov 22 to Nov 24, 2019
The city features 175 American artists and master crafters who compete in a number of talent areas. An annual event at the Royal Plaza Trade Center.
Festival of Trees - Methuen, MA - Nov 22 to Dec 7, 2019