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…

• Christmas at the Pentagöet: This December the inn brings a full array of Holiday entertainment. RSVP to any of the events bellow by calling 207-326-8616 or emailing stay@pentagoet.com:
  • December 1: The 2nd Annual Pentagöet Christmas Party! Bring a new unwrapped toy for our Toys-for-Tots drive and enjoy an open wine & beer bar at this swanky cocktail party. Festive attire encouraged!
  • December 2: Light Up Castine! Santa Claus is coming to town for one night only! Enjoy holiday shopping on Main Street, the Holly Berry Craft Fair, caroling on the town green, and the man in red himself! Free and open to the public.
  • December 3: Home Alone movie viewing. Join us for a special viewing of the holiday classic, with popcorn, hot cocoa, and wassail for the adults. (cost: $10pp)
  • December 8: Trivia Night, Castine Edition. The pub is open for a contest of who knows the most about our little town! Winner receives a Pentagoet gift certificate! (cost: $15pp + drinks)
  • December 9: Honey + Lace Baking Class. Join the Maine baker as she teaches us about how to step-up our holiday baking game! Perfect for bakers young and old to step-up their baking game in this interactive class. (cost: $55pp)
  • December 15: Trivia Night, Holiday Movie Edition. The pub is open for a contest of who knows the most about holiday movies! Winner receives a Pentagoet gift certificate. (cost: $15pp + drinks)
  • December 16: Miracle on 34th Street movie viewing. Join us for a special viewing of the holiday classic (cost: $10pp)
  • December 17: Holiday Sparkling Wine Tasting! Join Sigrid Coffin of Easterly Wines to learn about the best sparkling wines to adorn your table (cost: $65pp)
• Maine Maritime Academy Graduation is scheduled for Saturday, May 6, 2023. A celebration of the accomplishments of the Class of 2023, 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 2023. This excellent event takes place May 19-21 this year.
• Castine’s Memorial Day Weekend is the unofficial kickoff of the town’s summer season, from May 26-29! 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 June 1-4, 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 10-17 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 Friday, 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 2-3, 2023, with the opening party on the evening of the 2nd.  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 August 2-6 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 18-20, 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 2023, August 31-September 4.
• 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 9. Climb and learn about 20+ lighthouses throughout the state, including Castine’s own Dyce Head Light—for just one day.
• Maine Maritime’s Homecoming & Reunions is held September 30, 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.
• 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 22-24, 2023.
• 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 8 or 9, 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.
• Haunted Castine Ghost Tours! For the first time ever, 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.
• Halloween in Castine is a multi-day event to close out the Pentagöet’s final weekend of the season! Going from October 28-31, the inn hosts a giant, town-wide costume contest and potluck, with an open bar, aka HallowWINE (Sunday, October 29). On town green, kids can enjoy a trunk-or-treat… then come down to our haunted lobby for trick-or-treats, if they dare!
• Pentagöet Wine Tastings will be held on Saturday, October 21 & Monday, November 6. On the 21st, join sommelier Sara Nkemontoh for “Junk Food + Wine,” an entertaining look into pairing wines with your favorite late-night snacks. On the 6th, we’re hosting “Thanksgiving Wines” with André DiMattia of Blue Hill Wines. Find the best wines for your holiday table!

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!