From oyster festivals to sailboat races, Boothbay Harbor boasts a wide array of entertainment options that allow you to experience the lively local culture firsthand. No matter what time of the year you plan to visit, there are tons of upcoming events in Boothbay Harbor, ME. Topside Inn’s convenient location along the coast of Maine is close to the area’s best attractions. Before planning your getaway, be sure to request a complimentary copy of our Vacation Guide! It’s packed with local insight on even more events as well as restaurants, bars, and activities in the area.

Explore the Area!

Boothbay Harbor, ME, Upcoming Events and Festivals for 2019


  • Topside Inn Opening Day 2019 | May 3
  • Mother’s Day at the Coastal Maine Botanical Gardens (CMBG): Free admission for moms all day | May 12
  • Maine Days at the CMBG: Maine residents enjoy free admission. | May 25-27
  • Alewives Festival | May 25



  • Fourth of July: Enjoy activities and events throughout the town all day long followed by a spectacular fireworks display over the harbor, which guests can view from our lawn. We will provide fresh popcorn and other tasty treats during the show. | July 4
  • The Home & Garden Tour | July 19


  • Boothbay Harbor Fest: This waterfront event features local food, live music, and activities. | August 30-September 2 and September 7-8



  • Fall Foliage Festival at the Boothbay Railway Village | October 12-13

November & December

Year-Round Events

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.

Book the Best Accommodations in the Area

Room 14 at the Topside Inn

If you’re planning a trip to any of these outstanding Boothbay Harbor, ME, upcoming events, you’ll need to book a comfortable place to stay nearby. Topside Inn is a beautiful property close to all the best restaurants, attractions, and event venues in the area. Browse our list of accommodations including several beautiful rooms, a recently renovated suite, and a private cottage by the water. You’ll get to wake up to a delicious, homemade breakfast each morning before heading to the celebrations!