Gloucester Waterfront Festival - Glouceser, MA - Aug 15 to Aug 16, 2020
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.
Fluff Festival - Somerville, MA - Sep 12 to Sep 12, 2020
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!
BSV Oktoberfest - Walpole, MA - Sep 12 to Sep 13, 2020
Several thousand attend this two day Oktoberfest with German food, beer, games and even a full-contact medieval fighting exhibition. Location: 8 County St, Walpole, MA 02081
Swampscott Arts & Craft Festival - Swampsott, MA - Sep 12 to Sep 13, 2020
Annual arts & crafts show – free admission! Goes on rain or shine. Friendly leashed pets welcome.
Somerville Dog Festival - Somerville, MA - Sep 13 to Sep 13, 2020
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.
Boston Marathon - Boston, MA - Sep 14 to Sep 14, 2020
Due to COVID-19, the Boston Marathon has been postponed from April to September, but has since been moved to a virtual event, in response to concern about a second surge in fall, logistics, and health of runners and spectators (runners breathe harder than someone just standing, and social distancing with this popular marathon would be difficult). The famous 124th marathon harkens back to the 1897, after the success of the first marathon competition in the preceding year’s Olympics, making Boston the world’s oldest annual marathon, and it is one of six of the World Marathon Majors. About half a million spectators take in the marathon along the course, and about 30,000 runners participate every year.
South Shore Irish Festival - Marshfield, MA - Sep 19 to Sep 20, 2020
Enjoy live entertainment on multiple stages, corn hole tournament, tug of war competion, Irish magic show, Irish storytelling and more
Boston Latino International Film Festival - Boston, MA - Sep 23 to Sep 27, 2020
Annual event featuring films made by Latinos, about various themes and in different genres
Grotonfest - Gronton, MA - Sep 26 to Sep 26, 2020
Enjoy food, arts & crafts, and displays from local businesses and non-profits at Legion Common. Since 1979.
HUBweek - Boston, MA - Sep 30 to Oct 2, 2020
Bringing together individuals and organizations in pursuit of their mission – convening and celebrating the change makers doing impactful work at the intersection of art, science, and technology in Boston and beyond
Topsfield Fair - Topsville, MA - Oct 2 to Oct 12, 2020
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.
Harpoon Oktoberfest Boston - Boston, MA - Oct 2 to Oct 3, 2020
Oktoberfest has been going strong in fall at Harpoon in Boston for more than two decades. It includes Harpoon beer, German food, Oompah bands, chicken dancing, keg bowling game, and German chocolate cake-eating contest. Location: 306 Northern Avenue, Boston, MA 02210.
Honk! Festival - Somerville, MA - Oct 9 to Oct 11, 2020
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 17 to Oct 18, 2020
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 24 to Oct 25, 2020
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.
Boston Christmas Festival - Boston, MA - Nov 27 to Nov 29, 2020
Shop from 300 craft vendors just in time for the holidays. Admission is $14 with kids under 14 free. Held at the Seaport World Trace Center.