How to Have the Best Time at the Damariscotta Pumpkinfest

What are your plans for Columbus Day Weekend this year? If you want to take part in a fantastic fall festival, attend the Damariscotta Pumpkinfest. This highly anticipated celebration brings thousands of people together to kick off autumn in Midcoast Maine. Explore streets lined with pumpkin carvings, indulge in seasonal desserts, watch competitors go head to head in the pumpkin boat race, and so much more. 

Learn how to make the most of your time at the festival, and check out our free Vacation Guide to make the most of your entire experience in Midcoast Maine! We customized it with our recommendations on restaurants, shops, attractions, and more must-see events.

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5 of the Best Things to Do at the Damariscotta Pumpkinfest

1. View Unique Pumpkin Designs

Talented local artists create stunning displays along the streets of the downtown area every year to set the scene for the Damariscotta Pumpkinfest. They start with dozens of Atlantic Giant Pumpkins and transform them into remarkable works of art. Take a stroll through town and snap pictures with your favorites. Or, feel free to join the team of artists and add your design to the collection.

2. Enjoy Incredible Food

Bring your appetite because there’s always an abundance of delicious treats from the fall harvest. Help yourself to freshly baked pies, muffins, pancakes, and more. Of course, you can also find plenty of caramel apples. (It is a fall festival, after all!) If you know of a tasty pumpkin recipe, you’re invited to enter the Pumpkin Dessert Contest to win a variety of prizes.

3. Watch the Giant Pumpkin Parade

The Giant Pumpkin Parade is a favorite among locals and visitors alike. It features creative floats, decorated vehicles, and costumed marchers. Grab a spot along Main Street on Saturday and watch as they all travel past. It’s truly a sight to see!

4. See the Giant Pumpkin Drop

These giant gourds are carved, painted, raced, and eaten at the Damariscotta Pumpkin Festival. And, they’re even dropped from a crane stretching 180 feet high! Feel free to check out the action as pumpkins dive down and crash into junk cars. You can even watch catapults throw them through the air. Afterward, the pieces are collected and recycled as food for local farm animals!

5. Spectate the Pumpkin Boat Regatta

On Monday, excited attendees gather in the harbor to cheer on participants in the annual Pumpkinboat Regatta. Competitors hollow out giant pumpkins and either attach motors or use paddles to reach the finish line. If you want to relax in the shade but still catch the action, head over to the Lincoln Theater and watch it via a live stream.

Stay Nearby at the Topside Inn to Experience It All!

The bed inside Room 15 in the Windward Guest House at Topside Inn

If you need a place to stay so you can enjoy the full weekend of excitement, we invite you to join us in Boothbay Harbor at the Topside Inn. Breathtaking views, coastal-themed rooms, and fresh gourmet breakfasts are just a few of the things you can enjoy here. We even feature local artwork along our walls!

Among our list of top-notch accommodations is Room 15. Step inside to find a luxurious, king-size bed, vaulted ceilings, and an outdoor sitting porch where you can unwind and gaze out at the harbor.

Book your stay today for the ultimate vacation in Midcoast Maine. We look forward to seeing you at the Topside Inn!