Events and Festivals in Maine

Festivals & Events

Summertime in the Midcoast is a sea of exciting, uniquely Maine events! Our favorite is the Fourth of July in Castine when the whole town comes alive in an outdoor festival of activities, but starting in early May through late October, the whole area comes alive with county fairs, live music concerts, and one-of-a-kind experiences like the Maine Lobster Festival or the regional blueberry festivals. This is really the way life should be…

• Annual Pentagöet Easter Egg Hunt, hosted by Mister our mini schnauzer on Palm Sunday, March 24, from 2-3pm. Come hunt for colorful eggs left by the Easter Bunny (indoors or out, depending on weather). Mimosas for parents!
• Maine Maritime Academy Graduation is scheduled for Saturday, May 4, 2023. A celebration of the accomplishments of the Class of 2024, the town of Castine shakes off the winter chill for a weekend of excitement.
• “Wings, Waves & Woods”, the annual birding weekend hosted by the Island Heritage Trust in Deer Isle is back for 2024. This excellent event takes place May 17-19 this year.
• Castine’s Memorial Day Weekend is the unofficial kickoff of the town’s summer season, from May 24-27! On Memorial Day itself, our town hosts a ceremony befitting its military history with the tolling of the bells, speeches & remembrances, and a procession from town green to the water.
• The Acadia Birding Festival is scheduled for May 30-June 2, 2023,  and includes a Pelagic seabird boat trip, a wonderful birding opportunity. Keep an eye out for the regal penguins, unique to our area.
• The Guild School is an annual conference for the International Guild of Miniature Artisans, held on June 8-15 this year. These incredible artists make the smallest pieces of art ever… you’ve gotta see it to believe it!
• Castine’s Fourth of July is the quintessential Americana experience in Maine. The morning starts with a parade around town green, giving way to sack races, tug-o-war, and a blueberry pie eating contest. The Castine town band regales the locals in the afternoon, and a fireworks extravaganza sends the day out with a bang… And this year, the Pentagöet BBQ returns!
• Bastille Day in Castine is a one-of-a-kind experience on Sunday, July 14. Paying tribute to our founding as a French settlement in 1613, Main Street businesses fly the French flag, churches serve French toast breakfasts, and a giant Picnic en Blanc is held on Court Street, complete with live music and circus performers!
• Castine Classic Yacht Race, from Castine to Camden is hosted annually by the Castine Yacht Club. This year’s event takes place August 1, 2024, with the opening cocktail party on the evening of the 31st.  This 19.6nm race will be the first of three day races in conjunction with the Camden Classic Yacht Race to Brooklin and the Eggemoggin Reach Regatta.
• The Maine Lobster Festival is the state’s biggest and greatest celebration of our favorite crustacean, held in Rockland on July 31-August 4 this year. Complete with a giant parade (with the signature lobster float), the coronation of a sea goddess, and of course, lobster galore, you’ll be partying like a lob-STAR!
• The Machias Wild Blueberry Festival is one of several regional fairs celebrating the state’s favorite little fruit. This year’s 46th annual celebration is on August 16-18, full of artisans, food makers, and pie eating contests!
• The Blue Hill Fair is an old Maine county fair with traditional farm games, oxen and horse pulls, 4-H ribbon-award ceremonies, pig races, barrel relays on horse, and sheep dog trials. This is the origin of E.B. White’s Charlotte’s Web! Scheduled for Labor Day Weekend 2024, August 29-September 2.
• Haunted Castine Ghost Tours! The Pentagöet Inn and Castine Touring Company partner to present a spooky tour of our town’s ghosts & legends. Meet at the town dock, and end at the inn for cocktails. $45/adult; $30/kid, running from September through October, Fridays through Sundays only starting 9/13 through 10/31. Book HERE.
• Delicious Drag Dinner Show “You Bettah Werk!” On Sunday, September 8, the inn is hosting its first-ever drag dinner in partnership with Delicious Drag Divas of Bangor. All of our drag events have sold out in lightning speed—tickets are $30/pp for entry, and drinks/food will be available for the extravaganza.
• Maine Open Lighthouse Day is a beloved annual attraction that brings over 18,000 people to the state to view our most iconic of landmarks on a one-day-only event on Saturday, September 14. Climb and learn about 20+ lighthouses throughout the state, including Castine’s own Dyce Head Light—for just one day.
• The Common Ground Fair is organized by the Maine Organic Farmers and Growers Association and features organic produce, hand made products, livestock and music—think the giant farmers market of your dreams. It is located in Unity, Maine and draws people from all over the state and New England. Scheduled for September 20-22, 2024.
• Maine Maritime’s Homecoming & Reunions is held September 28, and the town comes alive with current students as well as alumni coming in for the weekend. The inn’s pub is always packed every night with folks reminiscing of the old college days.
• Damariscotta Pumpkinfest & Regatta—oh my gourd, this is the Midcoast’s funniest, quirkiest fest for the giant gourd. This year’s event is held on October 6 or 7, depending on weather. Get ready to scope out colossal pumpkins, decked to the nines, and watch the truly one-of-a-kind sight of Mainers paddling across the harbor in… that’s right pumpkins.
• Monstrous Cake Class with Pastry Chef Zac Young on Sunday, October 13, 5-7pm! Sprinkle master, Food Network personality, and expert Halloween cake extraordinaire Zac Young will be at the inn for a one-of-a-kind monstrous cake class. Tickets are $50pp—kid friendly!
• Halloween in Castine is a multi-day event to close out the Pentagöet’s final weekend of the season! On Sunday, October 27, the inn hosts a giant, town-wide costume contest and potluck, with an open bar, aka HallowWINE. Then from October 31-November 2, the inn hosts multiple Halloween-themed events. During the day of Halloween, come visit the Witch of the Pentagöet, Morgana, for storytime and treats. In the evening on the town green, kids can enjoy a trunk-or-treat… then come down to our haunted lobby for trick-or-treats, if they dare!
• Annual Pentagöet Christmas Party! On Friday, December 6, from 5-8pm, join our team to kick off the holidays in Castine. Come enjoy hors d’oeuvres, an open wine & beer bar, and warm company—just bring an unwrapped toy for our annual Toys-for-Tots drive!
• Light Up Castine with Santa Claus at the Inn on Saturday, December 7! This is the Castine Merchants Association annual fundraiser, and once again the Man in Red himself will be greeting kids young and old, bringing along his treasure chest and fresh gingerbread. This event is FREE and open to the public.
• Holiday Drag Brunch with the Delicious Drag Divas, on Sunday, December 15, from 11am-2pm. Join our favorite queens from Bangor for a holiday themed extravaganza—think Mariah, Cher, and more. We’ll be serving up brunch & cocktails to boot! Tickets are $30pp, 18+ only.

Whether you’re coming to the Midcoast for a festival or simply for some much-needed R&R, stay at our award-winning bed & breakfast—we cannot wait to welcome you to Castine!