Special Events and Activities to Point toward in 2020

May 22, 2020 - Opening Day of our 122nd Season at Ocean Point Inn for Lodging and Restaurant! Dinner served Daily until October 14th! Full Hot Breakfast Daily - Free for All Guests until Oct 14!

Memorial Day Weekend - May 22 - 25, 2020 - See Memorial Day Weekend Lodging Specials

May 25, 2019 - 7:30 PM Dancer Nic Gaveiss and Edinburgh. Harpist Maeve Gilchrist with Celtic harpist Natalie Haas & guitarist Yann Falquet at the Boothbay Opera House Box office 207-633-5159. The Opera House, 86 Townsend Avenue, Boothbay Harbor.

June 2, 2019 - 7:30 PM Ellis Paul, Red Molly’s Abbie Gardner with Seth Glier. Music starts @ 7:00 PM - Boothbay Opera House Box office 207-633-5159. The Opera House, 86 Townsend Avenue, Boothbay Harbor.

June 8, 2019 - 7:30 PM Caitlin Canty, singer songwriter - Boothbay Opera House Box office 207-633-5159. The Opera House, 86 Townsend Avenue, Boothbay Harbor.

June 14, 2019 - 7:30 PM The Brothers Brothers - Boothbay Opera House Box office 207-633-5159. The Opera House, 86 Townsend Avenue, Boothbay Harbor.

June 21, 2020 – Fathers Train Day - Boothbay Railway Village. Dad rides train free with child It’s another great day at the Village – but with a special twist. It’s Father’s Day! So lucky dads ride the train for free – simply because they are great dads! 586 Wiscasset Road, Route 27, Boothbay, ME 207-633-4727

June 21 - 29, 2020 - 58th Annual Windjammer Days -
Fully rigged windjammers sail into Boothbay Harbor. Two days, Tuesday and Wednesday, of family fun, pancake breakfasts, waterfront concerts, and fireworks over the Harbor, street parade, antique boat parade and more.

June 24, 2020 - Gathering of the Fleet - 1 - 3 pm -
While Windjammer Days in Boothbay Harbor offers a week full of events, it is the Windjammers who we have gathered to celebrate. They are each a vessel of living history and their entrance into the harbor each June is not only treasured by those who turn out year after year to watch, but they are also revered and respected for keeping an important piece of our past as part of our present. The Windjammers will gather off Cabbage Island to begin their glide into Boothbay Harbor under full sail. They will start arriving shortly after 1 pm.

June 24, 2020 - Windjammer Days Fireworks - 9:15 PM
Find a cozy establishment in the harbor, or stake your spot along the shore and watch the fireworks light the sky over the majestic masts of the windjammers! Town of Boothbay Standing Policy for Postponing Fireworks: If the weather for the scheduled night is bad, the fireworks will be postponed until the NEXT best evening. The decision will be made by the town manager and the pyrotechnics company by 6:00 PM. The fireworks will not be cancelled.

June 27, 2020 - Windjammer Days Lighted Boat Parade - 9:00 PM
Watch from anywhere in the inner harbor and make some noise to cheer on the fabulous mariners who have decorated their boats for your enjoyment! Have a boat and want to join in the fun? All are welcome! Boats rally at 8:45 pm. Parade enters the harbor shortly after 9 pm. Boats are scheduled to circle the inner harbor twice, unless otherwise instructed by the Harbor Master.

June 27, 2019 - Antique Boat Parade - Time: 3:00 PM - 4:00 PM - Antique Boat Parade around Boothbay Harbor ~ A site to see.

June 27, 2019 - 7:30 PM The Kruger Brothers - Boothbay Opera House Box office 207-633-5159. The Opera House, 86 Townsend Avenue, Boothbay Harbor.

June 28, 2019 - 7:30 PM Jerry Douglas & the Earls of Leicester - Boothbay Opera House Box office 207-633-5159. The Opera House, 86 Townsend Avenue, Boothbay Harbor.

Fourth of July - July 4th
30th Old Fashioned 4th of July Family Celebration. Arts & Crafts Show, children’s games, chicken barbeque, live music. Fireworks over the Harbor. Rain date: Next Best Day.

July 18, 2019 - 7:30 PM Tim Sample Maine humorist - Boothbay Opera House Box office 207-633-5159. The Opera House, 86 Townsend Avenue, Boothbay Harbor.

July 19, 2019 - 7:30 PM Professor Louie & the Crowmatix - Boothbay Opera House Box office 207-633-5159. The Opera House, 86 Townsend Avenue, Boothbay Harbor.

August 1, 2019 - 7:30 PM Tom Rush with Matt Nakoa - Boothbay Opera House Box office 207-633-5159. The Opera House, 86 Townsend Avenue, Boothbay Harbor.

August 9, 2019 - 7:30 PM Jig Jam Iris music with bluegrass - Boothbay Opera House Box office 207-633-5159. The Opera House, 86 Townsend Avenue, Boothbay Harbor.

August 10, 2019 - 7:30 PM Sons of Serendip - Boothbay Opera House Box office 207-633-5159. The Opera House, 86 Townsend Avenue, Boothbay Harbor.

August 15, 2019 - 7:30 PM The Subdudes - Boothbay Opera House Box office 207-633-5159. The Opera House, 86 Townsend Avenue, Boothbay Harbor.

August 22, 2019 - 7:30 PM Bob Milne ragtime - Boothbay Opera House Box office 207-633-5159. The Opera House, 86 Townsend Avenue, Boothbay Harbor.

August 23, 2019 - 7:30 PM Le Vent du Nord francophone folk - Boothbay Opera House Box office 207-633-5159. The Opera House, 86 Townsend Avenue, Boothbay Harbor.

Aug 30 - Sept 2 - Food Tastings and Live Music. A 3 day adventure for your senses! 16 Venues. Weekend Passport includes food tastings and live music at local restaurants for $15pp. An unforgettable weekend is guaranteed! Plus a Cold River Cocktail Competition. Part of the Boothbay Harbor Fest 9-Day Event - Voted Best New England Fall Events by Yankee Magazine

September 4 - 12, 2020 - Boothbay Harborfest - 8th Annual - Music, Food, Trail Run. Half Marathon, Art Sales, Trunk Shows, Photo Workshops, Fashion, Yoga, Spas, Hikes and More. Click Here for more details - schedule and tickets

September 6, 2020 - 5K Trail Run in Boothbay Region Land Trust Preserve. Part of the Boothbay Harbor Fest

September 6, 2020 - Half Marathon with miles of water views. Part of the Boothbay Harbor Fest

Sept 12, 2020 - Fishin' For Fashion Show - The Funkiest Fashion Show EVER! The show that marvels its audience year after year! Absolutely everything about this show is sea inspired and original! From the historic working waterfront venue, to the lobster trap runway that carries dozens of models the length of an enormous boat shed. The show celebrates local merchants, talented designers and Mainer's who dedicate their lives to preserving our working waterfront. Part of the Boothbay Harbor Fest

Sept 7 - 8 - East Side Vibe Fest on the Historic Working Waterfront. Ocean Point Marina, East Boothbay. Vinate and Artisan Barket, Food Trucks, Family Fun. Spectacular Live Music on the Waterfront Stage. Part of the Boothbay Harbor Fest 9-Day Event - Voted Best New England Fall Events by Yankee Magazine

September 26, 2020 –  Family Harvest Days - Boothbay Railway Village. 7th Annual. Special Discounted Pricing for the Day. A truly family focused event - with an emphasis on children. Barrel Train Rides. Hayrides. Face Painting. Pumpkin Painting. Sack Races. Kernel Digs. Haystack Climbing. Artisans, including Blacksmith, Cider Press, and Looming! And ... Prizes! 586 Wiscasset Road, Route 27, Boothbay, ME 207-633-4727

September 26 - 28, 2019 - Boothbay Charities Golf Classic - to benefit Maine Special Olympics - 29th year of this annual golf tournament. Lobster bake, sports auction, and play golf with a celebrity! All while helping those less fortunate to receive sports equipment and to give them opportunities to lead more fulfilled lives! $250 per golfer includes: lobster bake on Friday, September 27 at the Boothbay Railway Village followed by a sports memorabilia auction and the tournament itself on Saturday, September 28. Several celebrities will be staying at Ocean Point Inn. See Ocean Point Inn Specials

September 28, 2019 - 7:30 PM Seth Glier  - Boothbay Opera House Box office 207-633-5159. The Opera House, 86 Townsend Avenue, Boothbay Harbor.

October 4, 2019 - 7:30 PM Antonio Lopez & Friends - Boothbay Opera House Box office 207-633-5159. The Opera House, 86 Townsend Avenue, Boothbay Harbor.

October 5 – 14, 2019 - Damariscotta Pumpkinfest
Oct 10 - Damariscotta Pumpkinfest - Giant Pumpkin Deployment - After 3:45 p.m. - Main Street, Damariscotta & Newcastle.

October 11, 2019 - Kenari Quartet - Boothbay Opera House Box office 207-633-5159. The Opera House, 86 Townsend Avenue, Boothbay Harbor.

Oct 10 - Damariscotta Pumpkinfest - Giant Pumpkin Deployment - After 3:45 p.m. - Main Street, Damariscotta & Newcastle.

Oct 11 - Damariscotta Pumpkinfest - Giant Pumpkin “Artists at Work” – All Day

Oct 11 - Damariscotta Pumpkinfest - Carving & Painting – Main Street, Damariscotta & Newcastle. Pumpkinboat Building – All Day. Pinkham’s Plantation, 431 Biscay Road, Damariscotta

Oct 11 - Damariscotta Pumpkinfest - Don Brewer Blues Band * 7:00 p.m. – 10:00 p.m. (No Cover Charge) 436 Main Street, Damariscotta

October 9 - 12, 2020 – 53rd Annual Fall Foliage Festival - Maine Crafts, culinary booths, chowder, cheeses, chili, and home baked goods.  Two days of toe-tapping music and entertainment. There are steam train rides and antique autos on the grounds. Sponsored by the Boothbay Information Center and the Boothbay Railway Village on Route 27 (586 Wiscasset Road), Boothbay, ME 207-633-4727

Oct 12 - Damariscotta Pumpkinfest - Pumpkinboat Building – All Day. Pinkham’s Plantation, 431 Biscay Road, Damariscotta. Parking & Shuttle: Lincoln Academy & Great Salt Bay School - 9:00 a.m. - 5:00 p.m. (Suggested donation $1)

Oct 12 - Damariscotta Pumpkinfest - The Queen of Pumpkins on Her Throne - Most Excellent Majesty, Katharina Keoughan. 10:00 a.m. – 1:00 p.m. AND 3:00 p.m. – 4:00 p.m. - Main Street at Water Street, Damariscotta

Oct 12 - Damariscotta Pumpkinfest - Buskers & Street Performers - 10:00 a.m. – 11:45 a.m. - Theater Street, Damariscotta

Oct 12 - Damariscotta Pumpkinfest - Metropolitan Opera - “Turandot” – by Puccini * 11:45 a.m. – Pre-Opera talk by Morton Achter. 1:00 p.m. – 4:35 p.m. - ($25 adult / $23 members / $5 for 18 or under) - The Lincoln Theater, 2 Theater Street, Damariscotta

Oct 12 - Damariscotta Pumpkinfest - Pumpkin Derby Pit Crew – Axle Installation - 12:00 p.m. – 4:00 p.m. - First National Bank, 223 Main Street, Damariscotta

Oct 12 - Damariscotta Pumpkinfest - Official Damariscotta Pumpkinfest “Giant Pumpkin Parade” - 2:00 p.m. - Main Street, Newcastle & Damariscotta

Oct 13 - Damariscotta Pumpkinfest - Eighth Annual Pumpkin Derby - 9:00 a.m. – 11:00 a.m. - Elm Street Plaza – Weatherbird Hill, Damariscotta

Oct 13 - Damariscotta Pumpkinfest - Pumpkin Hurl - Catapult & Giant Slingshot Fun - 10:00 – 2:00 p.m. ($5 for 6 slingshot pumpkins) - CRCT’s Round Top Farm, 3 Round Top Lane, Damariscotta

Oct 13 - Damariscotta Pumpkinfest - Buskers & Street Performers - 11:00 a.m. – 2:00 p.m. - Theater Street, Damariscotta

Oct 13 - Damariscotta Pumpkinfest - Kid’s Pumpkin Hunt & 180’ Giant Pumpkin Drop
1:00 – 4:00 p.m. FREE CONCERT by The Nikki Hunt Band
1:00 – 1:45 p.m. Pre-register entrants for Kid’s Pumpkin Hunt
2:00 p.m. Kid’s Pumpkin Hunt (age 5 and younger)
2:30 p.m. Kid’s Pumpkin Hunt (age 6 and older)
Immediately followed by Giant Pumpkin Drop - CRCT’s Round Top Farm, 3 Round Top Lane, Damariscotta

Oct 13 - Damariscotta Pumpkinfest - The Horseshoe Crabs (Rock & Country Band) - 4:00 p.m. – 7:00 p.m. (No Cover Charge) - Schooner Landing, Main Street by the Bridge, Damariscotta

October 12, 2020 - Ocean Point Inn Closing Day for the Season

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