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May 2018
Free

Seedling Sunday

May 20 @ 9:00 am - 2:00 pm
Pinkham’s Plantation,
431 Biscay Road
Damariscotta, ME 04543 United States
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Atlantic Giant Pumpkin Plant Giveaway Each year over 600 FREE Atlantic Giant Pumpkin plants are given away during “Seedling Sunday”. Those seedlings become the grand daddies of the pumpkin patch and are featured during Damariscotta Pumpkinfest™ as pumpkinboat contestants…

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September 2018
Free

Volunteer Growers Weigh-off

September 29 @ 7:00 am - 12:00 pm
Pinkham’s Plantation,
431 Biscay Road
Damariscotta, ME 04543 United States
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The Volunteer-Growers’ Weigh-Off will measure your giant pumpkin for a shot at the amateur title! Drop off from 7:00 a.m. - 10:00 a.m. with Volunteer-Growers Weigh-off starting promptly at 10:00 a.m. An official Damariscotta Pumpkinfest™ Weigh-Off Entry Form must…

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Boothbay Railway Village – Family Harvest Days Saturday

September 29 @ 10:00 am - 4:00 pm
Boothbay Railway Village,
586 Wiscasset Road
Boothbay, ME 04537 United States
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Boothbay Railway Village – Family Harvest Days * Sponsor: Boothbay Railway Village The Boothbay Railway Village is a non-profit educational organization. Nowhere else in New England can you ride the rails behind an authentic steam locomotive surrounded by historic…

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Pumpkin Derby Pre-Registration

September 29 @ 10:00 am - 12:00 pm
Pinkham’s Plantation,
431 Biscay Road
Damariscotta, ME 04543 United States
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The Pumpkin Derby features small, non-motorized pumpkin racers (total weight not to exceed 20 pounds) that race on a 50 yard course in downtown Damariscotta. Entrants, who design, decorate and build the pumpkin racers, compete in three age groups:…

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Free

Great Pumpkin Commonwealth (GPC) Official Weigh-off

September 30 @ 7:00 am - 12:00 pm
Pinkham’s Plantation,
431 Biscay Road
Damariscotta, ME 04543 United States
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The official Great Pumpkin Commonwealth (GPC) weigh-off is the State of Maine’s largest weigh-off, featuring the jaw-dropping TOTAL PURSE OF $10,000 is sponsored by Damariscotta Pumpkinfest & Regatta™!   A bonus of$1,000 will be awarded for a New State Record…

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Boothbay Railway Village – Family Harvest Days Sunday

September 30 @ 10:00 am - 4:00 pm
Boothbay Railway Village,
586 Wiscasset Road
Boothbay, ME 04537 United States
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Boothbay Railway Village – Family Harvest Days * Sponsor: Boothbay Railway Village The Boothbay Railway Village is a non-profit educational organization. Nowhere else in New England can you ride the rails behind an authentic steam locomotive surrounded by historic…

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Lighthouse Legends & Lore Cruise

September 30 @ 2:00 pm - 5:30 pm
Maine Maritime Museum,
243 Washington Street
Bath, ME 04530 United States
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Lighthouse Legends & Lore Cruise * This cruise will depart from the Maine Maritime Museum. Cost: members $52/non-members $65/age 6-12 $42/under 6 $5 Sponsor: Maine Maritime Museum Full Event Schedule Here   * This is an “Unaffiliated Event” and is not sponsored by…

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October 2018
Free

Giant Pumpkin Deployment

October 4 @ 3:45 pm
Main Street,
Damariscotta, ME 04543 United States
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Full Event Schedule Here What a sight to behold! Dozens of Atlantic Giant Pumpkins loaded onto volunteered flatbed trucks –using forklifts lent by Hammond Lumber and Hammond Tractor - rumbling down Main Street!  These “Bad Boys” are real traffic…

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Bath Cemetery Tour

October 4 @ 4:00 pm
Maine Maritime Museum,
243 Washington Street
Bath, ME 04530 United States
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Bath Cemetery Tour * This cruise will depart from the Maine Maritime Museum. Cost: members $24/non-members $30/under 12 $12 Sponsor: Maine Maritime Museum Full Event Schedule Here   * This is an “Unaffiliated Event” and is not sponsored by Damariscotta Pumpkinfest. Damariscotta…

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Free

Artists at Work: Giant Pumpkin Carving/Painting Friday

October 5
Main Street,
Damariscotta, ME 04543 United States
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Each year, local Maine artists more than meet the challenge of decorating sixty to seventy Atlantic Giant Pumpkins which are displayed in downtown Damariscotta & Newcastle during Damariscotta Pumpkinfest & Regatta™. The results are extraordinary and bring thousands of viewers…

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Free

Pumpkinboat Building

October 5 - October 6
Pinkham’s Plantation,
431 Biscay Road
Damariscotta, ME 04543 United States
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Full Event Schedule Here Come and build your own pumpkin boat racer or watch the intrepid boat builders transform a giant pumpkin into a seaworthy vessel. The rules are "there are no rules and no fouls, other than that the…

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$20

Pumpkin Derby “Pit Crew” – Axle Installation

October 5 @ 12:00 pm - October 6 @ 4:00 pm
First National Bank,
223 Main Street
Damariscotta, ME 04543 United States
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Time to complete your pumpkin racer! The Pumpkin Derby takes place Columbus Day weekend and features small, non-motorized pumpkin racers (total weight not to exceed 20 pounds) that race on a 50 yard course in downtown Damariscotta. Sponsors: First…

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$5.00

Kent Axell, Magician

October 5 @ 7:00 pm - 8:30 pm
Lincoln Theater,
2 Theater Street
Damariscotta, ME 04543 United States
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The Lincoln Theater presents Kent Axell, live from Las Vegas! Sponsor: The Lincoln Theater Kent Axell is one of New York City's most in demand, fun and astonishing magician/ mentalists. Kent performs astonishing feats of mind reading, influence, and…

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Street Food

October 6 - October 8
Main Street,
Damariscotta, ME 04543 United States
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During the Damariscotta Pumpkinfest & Regatta™, the streets of Damariscotta/Newcastle  are filled with the smells of a variety of delicious offerings from downtown restaurants, as well as vendors and service clubs.  A wide array of food is provided throughout Saturday…

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CLC-YMCA Zombie Run & Kid’s Fun Run

October 6 @ 8:00 am - 11:00 am
CLC YMCA,
525 Main Street
Damariscotta, ME 04543 United States
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CLC-YMCA Zombie Run & Kid’s Fun Run * 8:00 a.m. - 9:00 a.m. Registration 9:15 a.m. Kid’s Fun Run 9:30 a.m. Adult 5K Zombie Run Sponsors: CLC-YMCA Full Event Schedule Here   * This is an “Unaffiliated Event” and is not…

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Free

InfoZone & Pumpkin Queen’s Throne – Saturday

October 6 @ 9:00 am - 4:00 pm
Water Street,
Damariscotta, ME 04543 United States
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Damariscotta Pumpkinfest™ “BUILDS COMMUNITY”, the InfoZone is held on the Saturday & Sunday of Columbus Day weekend. Sponsors: Coastal Maine Botanical Gardens During the InfoZone, local non-profits distribute literature about their organizations and inform visitors of their charter. It’s…

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$10.00

KidsZone and Kent Axell’s “School of Magic and Wizardry” Saturday

October 6 @ 9:00 am - 1:00 pm
KidsZone,
DRA's Darrows Barn
Damariscotta, ME 04543 United States
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Damariscotta Pumpkinfest & Regatta™ is all about the kids! Hundreds of volunteer “Squashbucklers” invest thousands of hours to ensure that free (or nearly free) family fun abounds during Pumpkinfest, from the weigh-offs at the beginning to the free matinee at…

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Boothbay Railway Village 51st Annual Fall Foliage Festival Saturday

October 6 @ 9:00 am - 5:00 pm
Boothbay Railway Village,
586 Wiscasset Road
Boothbay, ME 04537 United States
+ Google Map

Boothbay Railway Village 51st Annual Fall Foliage Festival * Sponsor: Boothbay Railway Village The Boothbay Railway Village is a non-profit educational organization. Nowhere else in New England can you ride the rails behind an authentic steam locomotive surrounded by…

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Free

Children’s Story Hour & Crafts

October 6 @ 10:00 am - 11:00 am
Skidompha Library,
184 Main Street
Damariscotta, ME 04543 United States
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The traditional Saturday Children’s Story Hour continues to be sponsored by Skidompha Library. Damariscotta Pumpkinfest & Regatta™ is all about the kids! Hundreds of volunteer “Squashbucklers” invest thousands of hours to ensure that free (or nearly free) family fun…

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Free

Buskers & Street Performers Saturday

October 6 @ 10:00 am - 11:45 am
Theater Street,
Damariscotta, ME 04543 United States
+ Google Map

Street performers will perform on Saturday, Sunday & Monday during Columbus Day weekend at Damariscotta Pumpkinfest & Regatta™ ! Numerous acts will take to the stage for the delight of visitors young and old throughout the weekend. With multiple…

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Free

Official “Giant Pumpkin Parade”

October 6 @ 2:15 pm
Main Street,
Damariscotta, ME 04543 United States
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Official “Giant Pumpkin Parade” Sponsor: Sullivan Tire & Auto Service Music & Hooping by The Nikki Hunt Band Interested in being in the parade? View the sign-up info here! Full Event Schedule Here **************************************************** The Royal House of Orange Queen…

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Free

Pumpkin Pie Eating Contests

October 6 @ 3:00 pm - 4:00 pm
Gallagher, Villeneuve & DeGeer,
181 Main Street
Damariscotta, ME 04543 United States
+ Google Map

Congratulations to the 2018 Winners! Click here for 2018 Pie Eating Contest results. The ever-popular Pumpkin Pie Eating Contest is held immediately following the Official Giant Pumpkin Parade (which begins at 2:15 p.m.) , on Saturday of Columbus Day weekend.…

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$5.00

Kent Axell, Magician

October 6 @ 7:00 pm - 8:30 pm
Lincoln Theater,
2 Theater Street
Damariscotta, ME 04543 United States
+ Google Map

Kent Axell, Live from Las Vegas! Sponsor: The Lincoln Theater Kent Axell is one of New York City's most in demand, fun and astonishing magician/ mentalists. Kent performs astonishing feats of mind reading, influence, and magic. From coast to…

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Pumpkin Pancake Breakfast

October 7 @ 7:00 am - 11:00 am
American Legion Hall,
527 Main Street
Damariscotta, ME 04543 United States
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Pumpkin Pancake Breakfast * Sponsor: Wells Hussey American Legion – Post 42, Ladies Auxiliary Join the local American Legion for a full breakfast before you set out on a fun day of activity, and of course it features pumpkin! $6…

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Free

Pumpkin Derby

October 7 @ 9:00 am - 11:00 am
Weatherbird Hill,
132 Main Street
Damariscotta, ME 04543 United States
+ Google Map

Congratulations to the 2017 Pumpkin Derby Winners. Click here for 2017 Derby results. The Pumpkin Derby features small, non-motorized pumpkin racers (total weight not to exceed 20 pounds) that race on a 50 yard course in downtown Damariscotta. Sponsors:…

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KidsZone – Sunday

October 7 @ 10:00 am - 2:00 pm
KidsZone,
DRA's Darrows Barn
Damariscotta, ME 04543 United States
+ Google Map

Full Event Schedule Here Damariscotta Pumpkinfest & Regatta™ is all about the kids! Hundreds of volunteer “Squashbucklers” invest thousands of hours to ensure that free (or nearly free) family fun abounds during Pumpkinfest, from the weigh-offs at the beginning…

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Free

InfoZone Sunday & Pumpkin Queen’s Throne

October 7 @ 10:00 am - 2:00 pm
Water Street,
Damariscotta, ME 04543 United States
+ Google Map

Full Event Schedule Here Damariscotta Pumpkinfest™ “BUILDS COMMUNITY”, the InfoZone is held on the Saturday & Sunday of Columbus Day weekend. Sponsors: Coastal Maine Botanical Gardens During the InfoZone, local non-profits distribute literature about their organizations and inform visitors of…

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Boothbay Railway Village 51st Annual Fall Foliage Festival Sunday

October 7 @ 10:00 am - 4:00 pm
Boothbay Railway Village,
586 Wiscasset Road
Boothbay, ME 04537 United States
+ Google Map

Boothbay Railway Village 51st Annual Fall Foliage Festival * Sponsor: Boothbay Railway Village The Boothbay Railway Village is a non-profit educational organization. Nowhere else in New England can you ride the rails behind an authentic steam locomotive surrounded by…

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Pumpkin Catapult & Giant Pumpkin Sling Shot Fun

October 7 @ 10:00 am - 2:00 pm
Round Top Farm,
510 Main Street
Damariscotta, ME 04543 United States
+ Google Map

Come watch Giant Pumpkin Sling Shot Fun at DRA’s Round Top Farm! Airborne pumpkins are an all natural source of fun at Pumpkinfest - whether sling-shotted, catapulted, dropped, trebucheted, or otherwise launched - so come see the gourds as they fly through the air.…

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Free

Buskers & Street Performers Sunday Afternoon

October 7 @ 11:00 am - 2:00 pm
Theater Street,
Damariscotta, ME 04543 United States
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Street performers will perform on Saturday, Sunday & Monday during Columbus Day weekend at Damariscotta Pumpkinfest & Regatta™ ! Numerous acts will take to the stage for the delight of visitors young and old throughout the weekend. With multiple…

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Free

Kid’s Pumpkin Hunt

October 7 @ 1:00 pm - 4:00 pm
Round Top Farm,
510 Main Street
Damariscotta, ME 04543 United States
+ Google Map

Think “Easter Egg Hunt” only in orange !! Each year over 300 Jack-be-Littles, hidden in the Damariscotta River Association’s field, wait to be discovered by excited youngsters participating in Damariscotta Pumpkinfest’s™ Pumpkin Hunt. Children’s prizes, generously donated by Renys…

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Free

Giant Pumpkin Drop

October 7 @ 1:00 pm - 4:00 pm
Round Top Farm,
510 Main Street
Damariscotta, ME 04543 United States
+ Google Map

Visitors can thrill to the sight of huge Atlantic Giant Pumpkins being dropped from a 180’ crane onto junk cars and into inflatable swimming pools.  In the green-spirit of recycling, the splattered pumpkin pulp is gathered for eventual pig feed…

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Free

Kid’s Free Matinee

October 7 @ 4:30 pm - 7:00 pm
Lincoln Theater,
2 Theater Street
Damariscotta, ME 04543 United States
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Kid’s Free Matinee – "Its the Great Pumpkin, Charlie Brown" 4:30pm movie - Limited seating on a “first come” basis - no tickets required Sponsor: The Lincoln Theater Come join the fun in the center of town and the…

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Giant Pumpkin Sling Shot Fun Monday

October 8 @ 9:00 am - 11:00 am
Round Top Farm,
510 Main Street
Damariscotta, ME 04543 United States
+ Google Map

Full Event Schedule Here Come watch Giant Pumpkin Sling Shot Fun at DRA’s Round Top Farm! Airborne pumpkins are an all natural source of fun at Pumpkinfest - whether sling-shotted, catapulted, dropped, trebucheted, or otherwise launched - so come see the gourds as they…

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KidsZone Monday

October 8 @ 10:00 am - 2:00 pm
KidsZone,
DRA's Darrows Barn
Damariscotta, ME 04543 United States
+ Google Map

Full Event Schedule Here Damariscotta Pumpkinfest & Regatta™ is all about the kids! Hundreds of volunteer “Squashbucklers” invest thousands of hours to ensure that free (or nearly free) family fun abounds during Pumpkinfest, from the weigh-offs at the beginning…

Find out more »
Free

Pumpkinboat Regatta

October 8 @ 12:00 pm
Damariscotta Harbor,
49 Main Street
Damariscotta, ME 04543 United States
+ Google Map

Full Event Schedule Here Sponsor: Colby & Gale/Phillips Power Products  Blessing of the Fleet 2018 Regatta Results The Regatta will take place when high tide allows each year. For 2018, that will be at 12:00 noon, with a Free Concert by…

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Free

Buskers & Street Performers Monday

October 8 @ 2:00 pm - 4:00 pm
Theater Street,
Damariscotta, ME 04543 United States
+ Google Map

Full Event Schedule Here Street performers will perform on Saturday, Sunday & Monday during Columbus Day weekend at Damariscotta Pumpkinfest & Regatta™ ! Numerous acts will take to the stage for the delight of visitors young and old throughout…

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Free

Kids FREE Movie Matinee

October 8 @ 2:30 pm - 4:00 pm
Lincoln Theater,
2 Theater Street
Damariscotta, ME 04543 United States
+ Google Map

"Captain Underpants: The Epic Movie" (PG) Come join the fun in the center of town and the kids can enjoy a free movie! Sponsored By: The Lincoln Theater Full Event Schedule Here

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