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Maine

BOOTHBAY

LOCAL FESTIVALS - BOOTHBAY HARBOR REGION

Website: boothbayharborwindjammerdays.org/kids-events
Calendar: boothbayharborwindjammerdays.org/schedule
Updated: June 1, 2026

UPCOMING EVENTS

WEEK OF JUNE 1 – 7, 2026

No events listed.

THURSDAY - 6/25
7:00am - 11:00am — Windjammer Fleet Leaves the Harbor fleet departure
9:00am - 5:00pm — Artists Alley artists alley
9:00am - 12:00 Noon — Boothbay Farmer’s Market farmer's market
10:00am - 2:00pm — U.S. Navy Exhibit navy exhibit
10:00am - 3:00pm — United States Coast Guard Station - Boothbay Harbor coast guard open house
SUNDAY - 6/21
9:00am- 4:00pm — R/C sailing competition at Spruce Point Inn watch the races
1:30pm — Blessing of the fleet blessing ceremony
6:00pm — Boothbay’s Got Talent local youths compete
7:00pm — Decorated Boat Parade boat parade
MONDAY - 6/22
10:00am - 12:00pm — Mysterious Harbor Tours: History, Legend & Lore Walking Tour history tour
1:00pm - 2:30pm — 8th Annual Windjammer Days Crab Cake Cook Off crab cake cook off
TUESDAY - 6/23
7:00am - 9:00am — Pancake Breakfast pancake breakfast
9:00am - 5:00pm — Pirate Coin forging pirate coin forging
10:00am - 1:00pm — Kids Alley crafts and activities
10:00am – 10:30am — Pirates of the Dark Rose Puppet Show puppet show
10:00am - 12:00pm — Windjammers for Wee Mateys pirate stories
11:00am - 1:00pm — Pirates Tortuga Open pirate bazaar
11:30am — Crudbeard’s Cannon Lessons cannon lessons
1:30pm — Hot dog eating contest eating contest
1:30pm - 3:30pm — Mysterious Harbor Tours: Boothbay Bites Walking Foodie Tour foodie tour
2:00pm — Pirates of the Dark Rose Weapon Show weapon show
3:00pm — Recruitment of Young Pirates young pirates
7:00pm — Navy Band Northeast Pops Ensemble community performance
WEDNESDAY - 6/24
10:00am - 11:00am — Pirates of the Dark Rose Tortuga Open pirate bazaar
10:00am - 12:00pm — Mysterious Harbor Tours: Joy Ride E-Bike Tour joy ride tour
10:00am - 3:00pm — Maine State Aquarium explore aquarium
12:00-1:00pm — Navy Band Northeast’s Jack Tar Brass Ensemble brass ensemble
12:00pm — The Battle for Boothbay Harbor battle reenactment
12:30pm — Lobster Eating Contest eating contest
1:00pm - 3:00pm — Gathering of the Fleet fleet gathering
2:00pm — Cod Fish Races cod fish races
2:00pm — Navy Band Northeast’s Crosswinds Woodwind Ensemble woodwind ensemble
4:00pm — Street Parade street parade
9:00pm — Fireworks Spectacular over the Harbor fireworks show
FRIDAY - 6/26
10:00am - 12:00pm — Mysterious Harbor Tours: Hidden Harbor E-Bike Tour hidden harbor tour
1:00pm - 2:30pm — Mysterious Harbor Tours: Boos & Brews Walking Ghost Tour ghost tour
4:00pm — Annual Vintage Boat Parade vintage boat parade
4:30pm - 7:00pm — Pier Party pier party
SATURDAY - 6/27
11:00am - 4:00pm — Boat Bar Party…come Skip, Tug & Be Merry boat bar party
11:30am -1:00pm — 21st Annual Orne's Candy Store International Rock-Skipping Contest rock skipping contest
1:00pm — Server Shuffle server shuffle
2:00pm — Tug Across The Harbor tug across harbor
4:00pm - 5:30pm — Mysterious Harbor Tours: Spooks & Spirits Walking Ghost Tour ghost tour
7:30pm — Lucy Wainwright Roche and Suzzy Roche mother daughter duo

Full schedule at boothbayharborwindjammerdays.org/schedule →

ALSO IN BOOTHBAY

Boothbay Railway Village Museum Coastal Maine Botanical Gardens Boothbay Region Land Trust Boothbay Parks and Recreation