Food and Drink Events
Vintage Boat Parade & Pier Party
Friday, June 28
Parade Begins At 4:00* PM (Free Event)
Pier Party 4:30-7:00 PM (Ticketed Event)
The Shipyard In Boothbay Harbor
If you cherish the beauty of old boats with all their character and history, then this is an event not to be missed! A fleet of vintage boats (25+ years old) will grace our harbor in a regal parade of vessels. Announcing of the parade is done so it is semi-broadcast throughout the harbor. Join us for the Pier Party at The Shipyard in Boothbay Harbor. Enjoy appetizers, drinks (full bar), view the vintage boats tied up at the docks, groove to some great live music, and new this year - enjoy a gathering of a vintage cars at the shipyard! If you have a vintage car and would like to participate, please fill out the entry form.
Tickets are $65 per spectator (cash or check only) which includes entry to the Pier Party event along with one drink ticket (beer/wine/soda). Additional drink tickets may be purchased at the event.
*Please note only cash/check can be accepted at the Pier Party.
Please note: There is no parking at the Shipyard for this event. The Shipyard, 120 Commercial Street, is located 0.2 miles from Whale Park, in a westerly direction on Commercial Street, it is a 4 minute walk. (500 paces, we checked!)
Parking is available at various locations around town. A free trolley will do pick up and drop off at this event for those parked at the Boothbay Region High School, 236 Townsend Avenue and the Howard Street Parking Lot, 11 Howard Street.
The 6th Annual Windjammer Days Crab Cake Cook Off
Monday, June 23, 2025
1:00 PM - 3:00 PM
Boothbay Harbor Inn
31 Atlantic Avenue,
Boothbay Harbor
Thank you to our generous sponsor for this event
You're invited! Come witness local chefs competing for the most mouthwatering crab cake in Boothbay Harbor judged by a celebrity panel. Sure to attract a crowd of foodies and spectators alike, this event will help support Windjammer Days.
A panel of judges will select a winner based on presentation/plating, taste and creativity and the use of Maine waters crabmeat. The judges will give a score out of ten for each criterion, 1 being inedible, 10 being excellent. A People’s Choice Award will also be presented.
Judges: Mitch Weiss, Cherie Scott and Mark Osborn
Participants: Brady’s (returning champs from 2023), Whale’s Tale, Mine Oyster and Newagen Seaside Inn
Tickets to the event are available on a first-come, first-served basis. Tickets are $50/person and are limited. Cash bar will be available.
Please click on the button below or scan the QR code to purchase tickets.
2024 winners - Judges Choice - Mine Oyster, Ralph Smith; People’s choice - Brady’s, Chef John and Sous Chef James
Boat Bar Party…come Skip, Tug & Be Merry
Chowder House
saturday, juNE 28, 2025
11:00 Am - 4:00 PM
22 Granary Way
A great venue from which to watch the Rock Skipping Contest, Tug Across the Harbor and new event this year…the Server Shuffle! There will be a maximum of 12 two-person teams, comprised of some of the finest local waiters and waitresses, to see who has the steadiest hands. They will carry (one-handed) a tray of filled water glasses, race across the footbridge and fill a bucket up to a certain line. First team to fill the bucket wins! There may be a prize for best costume….
The finest local waiters and waitresses compete in a race across the Footbridge to determine who has the steadiest hand while carrying a tray of drinks.
Tickets cover entry to the Chowder House and select food choices. Cash bar open serving beer, wine and specialty mixed beverages.
Thank you to our generous sponsors for this event:
hot dog eating contest
whale park
tuesday, juNE 24, 2025
1:30 PM
22 Granary Way
There will be 2 heats: one for kids, one for adults.
There will be 1st, 2nd and 3rd prizes for each heat.
$10 entry per person
For more information: duntonsdoghouse@gmail.com Sponsored and run by Dunton's Doghouse.
Hot dog contest was a huge success!
Congratulations to our winner Dylan Geyer great job!
Dustin Bibber coming in at 2nd place and Mike Walsh coming in 3rd. Thank you to everyone who participated!
Huge thank you to Mine Oyster ~ Raw Bar & Gathering Place for helping us steam the hot dogs and donating toward our prize winners!
Thank you Darrell Gudroe for being an awesome MC
Thank you to all our local businesses that donated a gift card for our winners:
Mine oyster & The Boat House Bistro - Robinson's Wharf & Tug's Pub - Kalers - Pier one pizza - The ice cream hut - Janson's Clothing - Sherman’s - Orne's Candy Store - Dolphin Mini Golf - Downeast Ice Cream Factory, Boothbay Harbor, Maine - Cozy's Dockside