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.

Rails, Tails & Ales: The Midcoast Craft Beer Festival – Visitors will enjoy great craft beer from Maine breweries, an outdoor car show, plus a family-friendly setting including steam train rides.

The Home & Garden Tour


Boothbay Harbor Fest – August 31 – September 9. On the waterfront, featuring local food, live music and events

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


Pemaquid Oyster Fest (Damariscotta)

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.


The OPERA HOUSE at Boothbay Harbor

Enjoy a performance at our historic opera house this season. Don’t forget, guests of Topside Inn receive VIP reserved seating – just let us know and we will confirm your seats.

February 15 – Scotty River Trio/Upstairs

February 23 – Primo Cubano

March 2 – We Banjo 3

March 9 – Open Mic/Upstairs

March 24 – Caribbean Night

April 19 – Scotty River Trio/Upstairs

April 21 – Asleep at the Wheel

May 5 – Duke Robillard Band

May 13 – Mother’s Day Concert with Kevin Kiley & Friends

May 26 – Rodney Crowell

June 1 – The Kruger Brothers

June 9 – Ellis Paul

June 21 – Rhiannon Giddens

June 23 – Newberry & Verch

July 11 – Yes Darling w/ Ryan Montbleau

July 13 – Molly Tuttle

July 17 – Daponte String Quartet

July 19 – The Bumper Jacksons

July 21 – Chanticleer

August 2 – Arsentiy Kharitonov

August 3 – The Lonely Heartstring Band

August 8 – Frollein Sax

August 15 – DaPonte String Quartet

August 17 – Physical Comedy –Rob Torres

August 23 – Ragtime Master Bob Milne

August 25 – Seth Glier

September 14 – Peppino D’Agostino

September 22 – Coig

September 29 – The Contenders

Updated 2/9/2018: More performances may be added.