Festivals near Gloucester, MA.

Harvard Fall Fest

• Nov. 1 - Nov 2, 2025
• 65 N Harvard St - Boston, MA USA

• Food / Wine / Beer

• $10 - $25

Get ready for the ultimate fall celebration — Harvard Fall Fest is coming to Harvard Stadium on Saturday, November 1st, from 12 PM to 5 PM, and it’s s ....

25th Annual New England Holiday Craft Spectacular

• Nov. 1 - Nov 2, 2025
• Starland Sportsplex and Fun Park - Hanover, MA USA

• Community (Local / Fair)

• $1 - $10

Get ready to kick off the holiday season in style at the New England Holiday Craft Spectacular, returning to the South Shore for its 25th year! Join u ....

Castleberry Fall Craft Festival

• Oct. 25 - Oct 26, 2025
• Shriners Auditorium - Wilmington, MA USA

• Community (Local / Fair)

• $1 - $10

The Castleberry Fall Craft Festival Returns to the North Shore! Celebrate the beauty of Autum at the Castleberry Fall Craft Festival, returning to th ....

SpicetoberFest: Spice. Culture. Food.

• Oct. 18 - Oct 18, 2025
• City Hall Plaza - Boston, MA USA

• Community (Family & Kids)
• Food / Wine / Beer
• Music
• Nightlife
• Seasonal (Oktoberfest)

• FREE!!

SpicetoberFest: Spice. Culture. Food. SpicetoberFest is Boston’s hottest fall celebration of bold local flavors and vibrant culture. Launching o ....

SpicetoberFest: Spice. Culture. Food.

• Oct. 18 - Oct 18, 2025
• City Hall Plaza - Boston, MA USA

• Food / Wine / Beer

SpicetoberFest: Spice. Culture. Food.SpicetoberFest is Boston’s hottest fall celebration of bold local flavors and vibrant culture. Launching on Octob ....

Boston Water Lantern Festival

• Oct. 18 - Oct 18, 2025
• George Lane Beach - Weymouth, MA USA

• $25 - $50

The Boston Water Lantern Festival is bringing people together for a celebration of light and community! This unforgettable evening will be filled with ....

1st Annual Budweiser Brewery Food Truck Festival! 

• Oct. 18 - Oct 18, 2025
• Budweiser Brewery Experience - Merrimack, NH USA

• $1 - $10
• $10 - $25

Get Ready for the 1st Annual Budweiser Brewery Food Truck Festival!  Join us on Saturday, October 18, 2025, from 12:00 PM-6PM, at the Budweiser ....

Monsterbash! A Blacklight DJ Dance Party!

• Oct. 17 - Oct 17, 2025
• 71 Quarry Rd - Acton, MA USA

• $1 - $10

This is an outdoor event. Rain cancels. ....

Boston Skelly Run

• Oct. 11 - Oct 11, 2025
• Boston - Boston, MA USA

• Holiday (Halloween)
• Holiday (Other)
• Outdoor / Recreation
• Seasonal (Fall)
• Sports / Fitness

• $50 - $100
• $100 - $250

Get ready to lace up your running shoes for the most spine-tingling fun run of the year "Skelly Run"!Inspired by the beloved 12ft Halloween decoration ....

Stardew Valley: Symphony of Seasons

• Oct. 5 - Oct 7, 2025
• Boch Center Wang Theatre - Boston, MA USA

• Music

• $25 - $50

Join us on a musical journey from your first day in the valley all the way to your arrival to the summit, with the brand-new STARDEW VALLEY concert Sy ....

Oktoberfest 5K at Mayflower Brewing in Plymouth, MA

• Oct. 5 - Oct 5, 2025
• Mayflower Brewing - Plymouth, MA USA

• Sports / Fitness

Join us for the 7th Annual Oktoberfest 5K! This festive 5K takes place on October 5, 2025, at America's Hometown Mayflower Brewing in Plymouth, MA! Br ....

Smuttynose Rockfest Half Marathon and 5K

• Oct. 5 - Oct 5, 2025
• Hampton Beach, NH - Hampton, NH USA

• Sports / Fitness

• $25 - $50
• $50 - $100

The 16th Annual Smuttynose Rockfest Half Marathon and 5K returns to Hampton, NH on Sunday, October 5, 2025. Join thousands of runners as you rock your ....

41st Annual Apple Harvest Day

• Oct. 4 - Oct 4, 2025
• Downtown Dover - Dover, NH USA

You haven’t experienced fall in New Hampshire if you haven’t been to Dover’s storied Apple Harvest Day. This daylong celebration of all thing autumnal ....

LEAP TA: Life Sciences 2025

• Sep. 29 - Oct 1, 2025
• Revere Hotel Boston Common - Boston, MA USA

• Health & Wellness

• $250+

Experience how leading life sciences organizations such as Pfizer, AbbVie, Edwards Lifesciences, and The Jackson Laboratory are revolutionizing the wa ....

National Coffee Day: Make It a Cafely Moment

• Sep. 29 - Sep 29, 2025
• Cafely - Stoughton, MA USA

• Food / Wine / Beer

• FREE!!

Have you ever wondered why a simple cup of coffee feels like a warm hug on a busy morning? On National Coffee Day, celebrated every September 29 acros ....

Cafely Roast Rally

• Sep. 29 - Sep 29, 2025
• Cafely - Portsmouth, NH USA

• FREE!!

Get ready to raise a mug and celebrate National Coffee Day on September 29, a day that brews up warmth, connection, and a whole lot of flavor across t ....

National Coffee Day Toast by Cafely

• Sep. 29 - Sep 29, 2025
• Cafely - Beverly, MA USA

• Nightlife

• FREE!!

Hey there, coffee lovers! Let’s raise a mug to National Coffee Day on September 29, a day that feels like a warm hug for everyone who finds comfort in ....

Cafely's Brew Love for National Coffee Day

• Sep. 29 - Sep 29, 2025
• Cafely - Hopkinton, MA USA

• FREE!!

Gather ‘round, coffee lovers, because National Coffee Day on September 29 is here to warm our hearts and fill our cups with joy! It’s a day to sip, sa ....

Sip, Brew, Celebrate with Cafely on National Coffee Day

• Sep. 29 - Sep 29, 2025
• Cafely - Lawrence, MA USA

• FREE!!

As the crisp autumn air settles in, National Coffee Day on September 29 arrives like an old friend, inviting everyone to pause and savor the rich, com ....

Cafely Presents: National Coffee Day Brew Fest 2025

• Sep. 29 - Sep 29, 2025
• Cafely - Lawrence, MA USA

• Food / Wine / Beer

• FREE!!

Hey there, coffee lover! Are you ready to raise a mug to National Coffee Day on September 29? What better way to celebrate than diving into the rich, ....

National Coffee Day Roast Fest with Cafely

• Sep. 29 - Sep 29, 2025
• Cafely - Lawrence, MA USA

• Food / Wine / Beer

• FREE!!

Hey there, coffee lover! Let’s brew up some excitement for National Coffee Day on September 29, a day to raise your mug to the rich, comforting ritual ....

Celebrate National Coffee Day with Cafely Mornings

• Sep. 29 - Sep 29, 2025
• Cafely - Dedham, MA USA

• Nightlife

• FREE!!

As National Coffee Day approaches on September 29, let’s come together to celebrate the rich, comforting brew that fuels our mornings and connects us ....

Find Your Blend: National Coffee Day with Cafely

• Sep. 29 - Sep 29, 2025
• Cafely - Manchester-by-the-Sea, MA USA

• FREE!!

Hey there, coffee lovers! As we gear up for National Coffee Day on September 29, I can’t help but feel a warm wave of nostalgia thinking about the cou ....

Fresh Roasts, Warm Moments with Cafely

• Sep. 29 - Sep 29, 2025
• Cafely - Dedham, MA USA

• Food / Wine / Beer

• FREE!!

Hey there, coffee lovers! Let’s raise a mug to National Coffee Day on September 29, a day to celebrate the brew that fuels our mornings, sparks our co ....

Morning Mood: National Coffee Day by Cafely

• Sep. 29 - Sep 29, 2025
• Cafely - Brockton, MA USA

• FREE!!

Get ready to raise a mug to the brew that brings us together—National Coffee Day is here on September 29, and it’s time to celebrate the rich, aromati ....