From oyster festivals to sailboat races, Boothbay Harbor boasts a wide array of entertainment options that allow you to experience the lively local culture at its best! Below, you will find a list of some of our favorite local events and festivals that you won’t want to miss on your next trip to Boothbay Harbor, Maine.



Windjammer Days


4th of July – Enjoy activities and events all day long followed by a spectacular fireworks display over the harbor. Guests at Topside Inn enjoy front row seats from our front lawn. We will provide fresh popcorn and other tasty treats.


Shipyard Cup – Super-yacht Regatta on the Coast of Maine


Pemaquid Oyster Fest (Damariscotta)

Boothbay Harbor Fest – September 1-10, 2017, Labor Day weekend. A 10-day celebration on the waterfront, featuring local food, live music and events

Claw Down


Fall Foliage Festival


Boothbay Festival of Lights – November – December. For reservation details at Topside Inn, click here.

Gardens Aglow at Coastal Maine Botanical Gardens – November – December. For reservation details at Topside Inn, click here.


31st Annual Harbor Lights Festival


Year-Round Events

Boothbay Region Land Trust events (all season)

Coastal Maine Botanical Garden events (all season)


For even more information on the best Boothbay Harbor, Maine events and festivals, as well as other fun attractions in the area, download our Free Vacation Guide or visit our Things to Do in Boothbay Harbor page.