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Damariscotta Pumpkinfest & Regatta in Maine

Named the “Best Fall Festival in Maine” by Travel and Leisure Magazine, the Damariscotta Pumpkinfest & Regatta in Maine draws visitors to Maine’s midcoast region for 10 days of fun in early October. The main events take place over the Columbus Day holiday weekend, October 8-11, 2021, when adults and children gather to witness the many entertaining and inventive ways the founders of the event have created to celebrate the humble pumpkin. This “must-see” event is the “talk-of-the-town” for guests of our beloved bed and breakfast in Newcastle, Maine.

Volunteers Make the Regatta Happen

What started as a simple mission to promote horticultural education to gardeners of all ages, the event has grown into a family-friendly celebration of all things pumpkin. Hundreds of volunteers form the backbone of the festivities, donating time and materials to ensure the success of this well-loved festival. The role of the volunteers spans the spectrum from engineers who build the pumpkin “boats” for the regatta to artists who sculpt and decorate pumpkins for display along the main streets of Damariscotta and Newcastle.

Growing Giant Pumpkins

Each spring free Atlantic Giant Pumpkin seedlings are distributed to enthusiastic growers who nurture them patiently throughout the growing season. Eventually the seedlings grow into giant pumpkins that can weigh anywhere from 200 to 1400 pounds. Seeds from those giants are carefully harvested and dried for planting the following year.

Regatta in the Media

The Damariscotta Pumpkinfest & Regatta captured the attention of the media, with wonderful reviews of the event appearing in news outlets across the country and around the globe. Videos of the pumpkin artists at work and the hilarious antics of the pumpkin boat captains racing in the regatta punctuate YouTube.

T-Shirt Designing Contest

One of the most celebrated features of the festival is the annual T-shirt design contest. Native Maine artists compete for the $500 cash prize for the winning design. T-shirts and hoodies featuring the winning design then become a treasured keepsake from each year’s festival.

Damarascotta River in the fall with tree and rocklined shores

Highlights of the Pumpkinfest Weekend

Though a variety of events take place throughout the 10-day festival, the highlights occur over the final weekend.

  • Pumpkinboat Regatta: Imagine a giant pumpkin hollowed out and outfitted with a motor or powered by paddle. Captained by volunteers, it’s a race to the finish from the town landing in Damariscotta.
  • Giant Pumpkin Parade: Floats and costumed paraders march through downtown Damariscotta along with the winning pumpkin from the weigh-off.
  • Pumpkin Derby: Miniature pumpkins decorated and tricked-out with wheels race the course to the finish line.
  • Pumpkin Dessert Contest: Bakers and chefs compete for the winning dessert and bragging rights.
  • Pumpkin Drop: Watch as a massive pumpkin is hoisted by crane high above an inflatable pool and then dropped to its untimely death.
  • Pumpkin Catapult: Who wouldn’t want to watch 20-lb pumpkins hurled hundreds of feet in the air only to smash to the earth.
  • Giant Slingshots: Kids of all ages take aim at targets with miniature pumpkins.

Be sure to mark your calendar for this time-honored Damariscotta Pumpkinfest & Regatta in Maine happening in October. You’ll be close to the action when you stay at the Newcastle Inn. Call us today and book your favorite room.

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