Boothbay Harbor, Maine Calendar of Events

Why not plan your visit to take advantage of some of these Boothbay Harbor events? The Flagship Inn is open all year 'round, so it is easy to book our guest rooms and suites during the event of your choice. You'll enjoy our true community spirit, from the Boothbay Yacht Club Regatta to the Rock Skipping Contest, and everything in between. Just contact us at 207-633-5094, and we'll be glad to tell you more about Boothbay, Maine events.

Things to Do in Maine Year-round

Our area is home to a full calendar of events that are enjoyed by residents and visitors alike. We present this calendar below to help you plan your travel to the beautiful Maine coast.

Calendar of Maine Festivals and Events


  • Fisherman's Festival - This festival salutes fishermen with events that include a codfish relay, trap hauling, a lobster-crate race, the Miss Shrimp Princess Pageant, and many other events. The boat parade and Blessing-of-the-Fleet Memorial Service are highlights of the festival.
  • Maine Photography Show


  • Lobster Boat Races
  • Boothbay in Bloom - The entire town celebrates the start of summer with special events and a canvass of colorful flowers displayed at local stores and restaurants.
  • Windjammer Days Festival - The harbor fills with windjammers for two days of celebration that includes concerts, parades, fireworks, an antique boat parade, the Best-of-the-Harbor Food Competition and more.


  • Fourth of July Fireworks
  • Rock-Skipping Contest
  • House-and-Garden Tour
  • Jazz-Festival Weekend
  • Antique Auto Days
  • Boothbay Railway Village becomes the home to more than 250 restored antique autos. A Sunday parade caps the event.
  • Boothbay Harbor Yacht Club Regatta and Leukemia Cup


  • Boothbay Boat-Builders Festival


  • Shipyard Cup


  • Fall Foliage Fair - Ride aboard antique autos and a steam train as New England explodes in the colors of autumn. Also enjoy culinary exhibits, chowder, baked goods, traditional Maine crafts, and plenty of entertainment.
  • Scarecrow and Pumpkins at the Gardens


  • Early-Bird Sale / P.J. Party - Wear your jammies and explore a shopper's paradise, starting at 6:00 a.m.


  • Harbor Lights Festival - Santa arrives by boat, and horse-drawn carriages offer rides through the town. We also light the Christmas tree, hold a craft fair, go caroling, and enjoy a remarkable lighted boat parade.
  • Winter Wonderlands Tour

For more information, including specific dates, just click here.


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