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 – July 15, 2017, 12:00 pm – 4:00 pm. 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 – July 21, 2017, 9:30 am – 4:30 pm. Tickets go on sale June 1st.


Sunflower Celebration benefiting Friends of Thai Daughters – Friday, August 4, 2017, 6:30 pm – 9:30 pm. This event has helped to prevent child trafficking and transformed lives since 2005. Visitors will enjoy food, drinks, a live auction, entertainment, and reverse raffle. Topside Inn will be donating a two-night stay for the live auction.

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.


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.

April 6 – Alliage Quintet (4 saxophones & piano – extraordinary)

April 20 – Scotty River Trio in the upstairs bar

April 22 – Annual Caribbean Night w/ Pan Fried Steel Drums

May 19 – Ballroom Thieves

June 3 – Francine Reed – of Lyle Lovett’s Large Band

June 8 – Gaelic Storm

June 10 – Frank Vignola & Vinny Raniolo

June 16 – Tommy Emmanuel

June 17 – Tom Rush

June 24 – Apil Verch

June 29 – Tim Sample

July 1 – Seth Glier

July 6 – Sharon Shannon

July 8 – Joan Osborne

July 13 – Alasdair Fraser & Natalie Haas

July 14 – Vienna Piano Trio

July 15 – The Subdudes

July 19 – Guy Davis, bluesman

July 20 – Girls, Guns & Glory

July 22 – Jim Messina & his Band

July 27 – Kevin Kiley & Friends

July 28 – Steep Canyon Rangers

July 29 – Cherish the Ladies

August 2 – Skerryvore

August 4 – Seldom Scene

August 5 – Frances Luke Accord

August 9 – Arsentiy Kharitonov

August 11 – Villalobos Brothers

August 17 – Breakers Jazz Bandd

August 19 – Ed Gerhard

August 23 – Bob Milne

August 24 – BeauSoliel avec Michel Doucet

September 1 – Marcia Ball

September 2 – Adam Ezra Group

September 8 – Raging Brass

September 14 – Rob Ickes & Trey Hensley

September 17 – Dougie MacLean

September 23 – Rodney Crowell

October 14 – The Bobs Farewell Tour

Updated 3/22/17: More performances may be added.