* All events held in downtown Boothbay Harbor unless otherwise specified * All events subject to change
June 25 and 26: 9 AM – 9 PM - Friends of Windjammer Days information tent - Shuttle maps, event schedule here.
SUNDAY, JUNE 23
1 PM - Boothbay Harbor Yacht Club One Design Race: Event held between the Boothbay Harbor Yacht Club (Rte. 27, W. Boothbay Harbor) and Tumbler Island buoy.
Noon - Arthur Webster Memorial Rock Skipping Contest: At the footbridge parking lot. Bring your best seven (at least) chukkars. Each person has three skims. Four divisions for all ages. Registration: $5 (cash/check) collected on site. Prizes!
1:30 PM - Blessing of The Fleet: Best viewing around the inner harbor, Fishermen’s Memorial Park (Atlantic Avenue).
2 PM – Red Cloak History Tour – Special Maritime tour! Pre-registration required. Call 207-380-3806 .
6-9 PM – Reggae cruise with Dani Tribesmen – Cap’n Fish’s Red Ticket booth, Pier 1.
MONDAY, JUNE 24
1-3 PM - 2nd Annual Windjammer Days Crab Cake Cook Off! Boothbay Harbor Oceanside Resort. Atlantic Avenue. Limited to 40. Reserve your spot: 633-4455.
2-4 PM- Open House at the Boothbay Sea and Science Center: 216 Ocean Point Rd., East Boothbay. Experience this innovative program where no child is left sitting at the dock!
2-4 PM - Nathaniel Wilson Sailmakers Tours: 216 Ocean Point Rd., East Boothbay. Wilson is known worldwide for his expansive knowledge of sailmaking and rigging.
3 PM - Tug of War Across The Harbor: Footbridge parking lot.
4-5 PM - Ernestina-Morrissey Reception: 120 Commercial St. Visit her in dry dock. 100% of donations benefit the Ernestina-Morrissey Association.
4:30-6:30 PM - Linekin Bay Resort Tasting Event: 92 Wall Point Rd. With Cruzan rum. Over 21 only.
6 PM – Boothbay’s Got Talent – YMCA, 261 Townsend Ave. Admission $5. Up to 15 youth compete for titles of Miss Windjammer and King of the Harbor.
TUESDAY, JUNE 25
7-10 AM - Pancake Breakfast: Whale Park, Commercial Street
10 AM – 1 PM - Kids Alley: Boothbay House Hill Road
10-10:30 AM - Pirate Puppet Show: Whale Park, Commercial Street
10 AM – 3 PM - Windjammers for Wee Mateys: Activities, crafts, stories for the kiddos; Maine State Aquarium touch tank (til 2 p.m.) Boothbay Harbor Memorial Library, 4 Oak St.
10 AM - 4 PM - Tours of the U.S.C.G. Station: McKown Point Road, W. Boothbay Harbor. A free shuttle stop
10 AM - 4 PM - Maine State Aquarium: Crafts, activities, tours, fishing, more … McKown Point Road. A free shuttle stop
11 AM – Noon - Tours of the Must Roos pirate ship: Docked at Pier 6 at Fisherman’s Wharf
12:30 -1:30 PM – Pirate Duels and Oreo the Pirate Bird: Whale Park, Commercial Street.
1 PM - Red Cloak History Tour – Special Maritime tour! Pre-registration required. Call 207-380-3806.
1:30 - 3 PM - Recruiting for Pirates: At the Kid's Tent, Boothbay House Hill Road.
2-4 PM - Concert: Meghan Clark: Whale Park stage, Commercial Street
3-4 PM – Tours of the pirate ship Must Roos: Docked at Fisherman’s Wharf Inn
4-5 PM - Concert - Owen Kennedy: Whale Park stage, Commercial Street
5:15-6:30 PM – Concert - Boothbay Region Community Band: Whale Park stage, Commercial Street
7-9 PM - Concert - Gina and The Red Eye Flight Crew: Whale Park stage, Commercial Street
7:30 PM - Red Cloak Haunted History Tours: A lantern-lit walking tour. Pre-register for meeting place and tickets. Call 380-3806 or visit http://redcloakhauntedhistorytours.com
7:30 PM – Concert - Gaelic Storm: Concert at the Opera House 86 Townsend Ave. Tickets & info: 633-5159 and https://boothbayoperahouse.com
WEDNESDAY, June 26
Competition Day! Sign up for the lobster eating contest and/or Codfish relay race at the Friends of WJD info tent in the Whale Park.
7-10 AM - Pancake breakfast: Whale Park, Commercial Street.
9 AM-4 PM - Deck tours of Schooner Bowdoin. Bristol Marine, 120 Commercial Street.
9:30-10 AM - Pirate weapons demo: Whale Park
10 AM-3 PM - BRLT Kids tent: Activities, crafts, etc., Boothbay House Hill Road.
10 AM-3 PM - Maine State Aquarium: Crafts, activities, tours, fishing, more … McKown Point Road. A free shuttle stop.
10 AM-4 PM - Tours of the U.S.C.G. Station. McKown Point Road, W. Boothbay Harbor. A free shuttle stop
10:30-11:15 AM – Cannon lessons/Pirate shoot out: Whale Park, Commercial Street.
High Noon – British invasion/Attack on Boothbay Harbor! Town Landing/Whale Park
12:30 PM – Lobster eating contest: Whale Park, Commercial Street. Sign up at the event or at the Friends of WJD info tent. Open to all! $20 pp. A Festival FUNdraiser.
1-3 PM – The Gathering of the Fleet! The visiting schooners gracefully glide into the Harbor. Whale Park.
1-3 PM – Pirate duels and Oreo the pirate bird: Whale Park, Commercial Street.
2 PM – Fish relay races: Commercial Street. Open to all! Teams of four. Sign up at Friends of Windjammer Days info tent. Prizes!
2:30-4 PM – Concert - Dave Gagne Band: Whale Park stage, Commercial Street.
4-5 PM – Street Parade: Route begins at the high school on Townsend Ave., up toward Commercial Street.
5-6:45 PM – Concert - Windjammer Princess(es) and King of the Harbor: The youth crowned at Boothbay’s Got Talent show Monday night.
7-9 PM – Concert – Pat Colwell & the Soul Sensations: Whale Park stage, Commercial Street
7:30 PM – Red Cloak Haunted History Tour: A lantern-lit walking tour. Pre-register for meeting place and tickets. Call 380-3806 or visit http://redcloakhauntedhistorytours.com
9:15 PM – Fireworks - Best viewing anywhere around the Harbor; Whale Park, Footbridge, Fishermen’s Memorial Park (Atlantic Avenue).
THURSDAY, JUNE 27
10 AM - 2 PM – The Age of Fishing Under Sail: Boothbay Region Historical Society, 72 Oak St. Excellent exhibition!
1 PM – Windjammer Days Golf Tourney: Boothbay Harbor Country Club, Country Club Road, Boothbay. Open to all! Shotgun start. FMI: The country club: 633-3673 or Dianne:504-0242.
1 PM – Red Cloak History Tours – Special Maritime tour! Pre-registration required. Call 207-380-3806.
3 PM – Antique Boat Parade: Around the inner and outer harbor. Public reception follows at Oceanside Resort, Atlantic Avenue.
7-9 PM – Concert – The Work Trucks: Whale Park stage, Commercial Street
7:30 PM - Red Cloak Haunted History Tour: A lantern-lit walking tour. Pre-register for meeting place and tickets. Call 380-3806 or visit http://redcloakhauntedhistorytours.com
7:30 PM – Concert - Kruger Brothers: At the Opera House, 86 Townsend Ave. Tickets: 633-5159 and https://boothbayoperahouse.com
FRIDAY, JUNE 28
9 AM - 5 PM – Artists Alley & Silent Auction: Whale Park, Commercial Street. Rain date: Sept. 29.
10 AM - 2 PM – The Age of Fishing Under Sail: Boothbay Region Historical Society, 72 Oak St. Excellent exhibition!
11 AM - 2 PM – Concert – Ben Betts: Whale Park stage, Commercial Street
1 PM - Red Cloak History Tours – Special Maritime tour! Pre-registration required. Call 207-380-3806.
2-4 PM – Concert – Delta Knights Jazz Duo: Whale Park stage, Commercial Street
4-6 PM – Tour Schooners Adventure and Harvey Gamage. Tours and reception, Carousel Marina and Whale’s Tale, 125 Atlantic Ave. Meet the captains and crews and hear about their adventures.
6-8 PM – Sail on the Harvey Gamage: A fundraising trip. $75 pp. Reserve your tickets at: https://tallshipsportland.starboardsuite.com
7-9 PM – Concert – Don Brewer Blues Project: Whale Park stage, Commercial Street
7:30 PM – Concert – Jerry Douglas & the Earls of Leicester: Opera House, 86 Townsend Ave. Tickets: 633-5159 and https://boothbayoperahouse.com
SATURDAY, JUNE 29
7-11 AM – Pancake breakfast: At Edgecomb Fire Dept., 473 Boothbay Rd./Route 27. Donations accepted. FMI: 882-4060.
8 AM – Rocky Coast Road Race - 10k run, 5krun or 5k walk. A YMCA fundraiser for cancer survivor programming. Sign up at the Y, 261 Townsend Ave. FMI: 633-2855 or www.boothbayregionymca.org
10 AM - 2 PM – The Age of Fishing Under Sail: Boothbay Region Historical Society, 72 Oak St. Excellent exhibition!
1 PM - Red Cloak History Tours – Special Maritime tour! Pre-registration required. Call 207-380-3806.
6:30-9 PM – Concert – Dyer Neck Gang: Whale Park stage, Commercial Street
9 PM – Lighted Boat Parade: Boats parade around the inner and outer harbor. A grand finale to the Festival