The Iconic Damariscotta Pumpkinfest & Regatta Returns for 2021
The Pumpkins Return
The coastal town of Damariscotta is home to one of Maine's most unique festivals; Damariscotta Pumpkinfest & Regatta. Sadly due to the pandemic, the town had to skip the fun festivities but they're all-in for 2021.
I have a personal love for the event being from the area and in recent years having the opportunity to participate in the hilarious and harder than it looks regatta.
The event is held between October 7th and 11th.
Main Street in Damariscotta will be lined with giant pumpkins starting on Thursday, October 7th. The next day artists will start their masterpieces. These pumpkins get completely transformed by painting them and carving them. Pumpkins tell stories, feature iconic characters, and are incredibly Insta-worthy.
Pumpkin Parade and Activities
On Saturday is the giant pumpkin parade down Main Street. Leading up to the parade you can see the pumpkinboats being built, enjoy street performers, and bring the kids to the KidsZone.
A personal favorite event is the Giant Pumpkin Drop. Ever wonder what would happen if you dropped a giant pumpkin from a really high place? Well, wonder no more as a crane is on-site to lift a giant pumpkin high in the sky only to drop it onto a car or in years past, into a swimming pool. You won't believe the thud it makes!
The main event happens on Monday, October 11th. People travel from all across the country to witness and participate in the Pumpkinboat Regatta.
There are multiple heats, including one with your favorite Maine meteorologists, where participants climb into a giant pumpkin and paddle their hearts out for glory. Well, bragging rights and a trophy. (I don't mean to brag but in 2019 I got 3rd place. There were only 3 participants but that's just a minor detail.)
And yes, there are costumes!
After the heats of paddlers come the pumpkinboats with outboard motors!
This free event is truly fun for the whole family. Get more information here.