The Best Upcoming Events In New England: October 2021

Summer ending doesn’t have to be a bummer. Fortunately, New England has plenty of events to kick off the autumn season. From Oktoberfests and farmers markets to athletic endeavors, we’ve rounded up some of the best upcoming events in New England this October.

Martha’s Vineyard Oyster Festival

Martha’s Vineyard Oyster Festival is running between September 30 and October 2.
At the time of publication tickets are still available for Thursday’s events. 

Jack-O-Lantern Spectacular

The annual Jack-O-Lantern Spectacular hosted nightly by the Roger Williams Park Zoo is one of the best upcoming family-friendly events in New England. Operating dates run between September 30 and October 31. 

Harpoon Octoberfest

the best upcoming events harpoon octoberfest

Arguably one of the best upcoming events in New England is the annual Harpoon Octoberfest. This year’s festivities are taking place on October 1 and 2. For those interested in Dogtoberfest, that’s taking place on Sunday, October 3. 

Honk Fest

Get to Davis Square the weekend of October 8 and watch social activism and music meet. Over 15 street bands are set to perform at this year’s Honk Fest.

Damariscotta Pumpkinfest & Regatta

Last week the Damariscotta Pumpkinfest & Regatta released their strategy for this year’s scaled back events. Giant decorated pumpkins will still be displayed along Main Street between October 8 and 18. All other happenings have been suspended at this time.

White Mountain Oktoberfest 

Head up to Lincoln, New Hampshire between October 9 and 10 for a two-day Oktoberfest celebration. Indoor and outdoor beer gardens, live entertainment, family-friendly activities, and keg competitions await. Admission is free and hosted by Loon Mountain Resort.

Providence River Cruise

best upcoming events in new england twilight river cruise

Boating season is winding down. Hop aboard an end-of-season Twilight River Cruise hosted by Providence River Boat Company before October 15. 

At the time of publication, WaterFire Boat Rides are still available on the following dates: October 2, October 16, and November 6. 

Go Apple Picking

Stock up on all your apple essentials at one of the many orchards located around New England. Apple picking season has already started and runs through early November. 

2021 Boston Marathon

Typically held in April, the 125th Boston Marathon is now taking place on Monday, October 11. 

Head of the Charles Regatta

the best upcoming events head of the charles

The 55th Head of the Charles Regatta is taking place between October 22 and 24. Spectators click here to check out the vantage points. 

Farmers Markets

Boston Public Market at Dewey Square

Open Thursdays from 11:00am and 6:00pm now until November 18.

Portland Farmers Market

portland farmers market

Open Wednesdays and Saturdays from 7:00am until 1:00pm in Deering Oaks Park.
Fun Fact: the Portland (Maine) Farmers Market has been in business since 1768. 

Salem, Massachusetts


We all know Salem is *the* place to spend an autumn day in New England. Events are scheduled daily throughout the town. Keep in mind that Salem gets busier as Halloween gets closer. 

$35 Thursdays at Sugarbush Golf Club

Golfers in Warren, Vermont can take advantage of discounted green fees at Sugarbush Golf Club. Foursomes can play for just $35 per person on Thursdays after 11:00am.