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Boothbay Harbor 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 Windjammer Days in June to the Gardens Aglow in December, and everything in between. Just contact us at 207-633-5094, and we'll be glad to tell you more about Boothbay, Maine events.

Calendar of Festivals and Events

  • 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
  • House-and-Garden Tour
  • Antique Auto Days
  • Rails Tales & Ales at Boothbay Railway Villiage
  • Maine Stone Symposium Boothbay Railway Villiage
  • Harborfest
  • Firefighters Convention
  • 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.
  • Early-Bird Sale / P.J. Party - Wear your jammies and explore a shopper's paradise, starting at 6:00 a.m.
  • Gardens Aglow
  • 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.