What Are the Best Boothbay Harbor Festivals?

Boothbay Harbor, Maine, is a year-round vacation destination. Whether you’re visiting in the winter, spring, summer, or fall, there’s always something going on. From food festivals and concerts to holiday celebrations, our seaside village offers an exciting array of events in every season. Here are some of our favorites, and this list is just the start. Learn more about Boothbay Harbor festivals and other fun things to do when you download our free Vacation Guide. Inside, you can find more upcoming events, local tips, and best-kept secrets to make your Maine getaway the best it can be.

Make the Most of Your Visit

Join the Excitement at the Best Boothbay Harbor Festivals

Windjammer Days | June

People enjoying a schooner ride: a favorite activity on our Maine Vacation Itinerary

Kick off the summer in Boothbay Harbor at Windjammer Days, an annual festival that showcases our region’s maritime history. Each year, over 40 antique ships line our harbors and offer visitors an inside look at windjammers from the 19th and early 20th century. Parades, fireworks, a lobster eating contest, and other exciting events round out the festival. It’s been a local favorite for over half a century and shows no sign of slowing down.

After marveling at these spectacular ships, set sail on a boat cruise of your own. Check out some of the best boat tours Boothbay Harbor has to offer and explore the beauty of Midcoast Maine.

Boothbay Harbor Fest | September

Boothbay Harbor Fest is one of the most anticipated events of the year. This popular celebration brings locals and visitors together for ten days of Maine’s famous food, music, and art. One of our favorite Boothbay Harbor Fest events is the half marathon, which takes runners of all abilities on a journey from the inner harbor to the open ocean. The scenery and natural surroundings are nothing short of spectacular. After your run, treat yourself to some tasty bites or a unique souvenir from local vendors.

Claw Down | September

Appetizer from Claw Down in Boothbay Harbor

No trip to Maine is complete without some of our fresh, boat-to-table lobster. At the Claw Down in Boothbay Harbor, top chefs create buttery delights out of 2,500 lobsters from local wharves. And, you’re invited to sample their savory offerings and cast your vote for the People’s Choice Award. With such a wide range of delicious options, it’s often difficult to choose. You can even pair your lobster dish with a locally-brewed beer or glass of wine. One thing is for sure — after this Boothbay Harbor event in September, you’ll leave with a full stomach and a craving to come back for more.

Don’t Miss out on More Must-See Festivals Throughout the Area

Boothbay Food & Music Festival | September

The friendly competition at the Claw Down marks the start of an even bigger celebration of Midcoast Maine’s cuisine and culture. The first-annual Boothbay Food & Music Festival was a massive success in 2018, and there’s much more to come. Previous activities have included gourmet dinner parties, dancing under the stars, and antique car shows. Check it out in September for three fun-filled evenings.

Pemaquid Oyster Festival | September

Shucked oysters at the Pemaquid Oyster Festival

Held each year in Damariscotta, ME, the Pemaquid Oyster Festival celebrates the famous Pemaquid oysters. Enjoy them fried, baked, or on the half shell with a great lineup of musicians and live entertainment as a backdrop. Be sure to stick around for the shucking contest, too. If you weren’t already convinced to attend, the proceeds also benefit the community with marine conservation efforts.

Fall Foliage Festival | October

If you’ve ever visited Maine in the fall, you know the vibrant foliage is something worth celebrating. The annual Fall Foliage Festival at Boothbay Railway Village is the perfect opportunity to immerse yourself in this stunning scenery. Every Columbus Day weekend, this event welcomes dozens of vendors and a wide variety of performers. Festivities include:

  • Steam train rides
  • Artist demonstrations
  • A pumpkin carving contest
  • Craft shows
  • Live music
  • And more

Boothbay Lights Festival | November – December

Couple at a holiday festival during Christmas in Maine

As we approach the holiday season, Midcoast Maine comes alive with joyous celebrations around every corner. They’re all part of the Boothbay Lights Festival, where holiday cheer fills the community and warms the hearts of locals and visitors alike.

One of the many must-see events during the festival includes the largest light show in Maine. At Gardens Aglow, hundreds of thousands of twinkling lights showcase the unparalleled beauty of the Coastal Maine Botanical Gardens. In addition to the dramatic display, you can enjoy exceptional food and beverage options, holiday shopping in the garden’s gift shop, and s’more roasting over a crackling bonfire. It’s the perfect way to get in the spirit of the holidays.

Stay at Topside Inn to Enjoy These Delightful Celebrations

View of Room 8 at Topside Inn

If you’re planning to attend an upcoming festival in Boothbay Harbor, ME, there’s no better place to stay than Topside Inn. Our coastal bed and breakfast features charming guest rooms and unbeatable, panoramic views of the waterfront. We even serve gourmet breakfasts every morning with fresh, local ingredients.

Room 8 is just one of many luxurious rooms you can find at Topside Inn. This private, beautifully appointed space includes original paintings from a local artist, an inviting king-size bed, and a spacious deck with remarkable views of the harbor. After one night here, you won’t ever want to leave.

If you’d like to experience the beauty of Boothbay Harbor, check our availability and reserve your room today. You can even get a taste of what it’s like to stay with us before booking with our virtual tours. We hope to see you soon.