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 pumpkin needs to float and needs to go really fast”! Described as the “extreme sport of gardening,” this real-life jack-and-the-beanstalk sport has been seen by over 30,000 fans. Visitors have flocked to Damariscotta to watch giant gourds -steered by captains either paddling or powered by “wicked nice motors”- ply the waters of the Damariscotta River.

Damariscotta Pumpkinfest™ “BUILDS COMMUNITY”, the InfoZone is held on the Saturday & Sunday of Columbus Day weekend.

During the InfoZone, local non-profits distribute literature about their organizations and inform visitors of their charter. It’s a terrific way for local service organizations to communicate their goals to the community. In addition they can raise needed funds to further their service objectives by selling items that are directly related to their own operation, such as raffle tickets, T-shirts, pins, hats, etc.

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 abounds during Pumpkinfest, from the weigh-offs at the beginning to the free matinee at the end.

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 the end.

KidsZone Sponsor: Tidewater Telecom

Queen’s Throne Sponsor: Phelps Architects

The KidsZone activities & events will be held on Columbus Day weekend (Saturday, Sunday and Monday) during Pumpkinfest, from 10:00 a.m. – 2:00 p.m. daily.

Families with children of all ages can enjoy the giant pumpkin bounce houses and the inflatable giant-slide, family photographs surrounded by Atlantic Giant Pumpkins & hay bales (think: “holiday cards” !!), temporary tattoos, face painting, sand treasures, pick-a-pumpkin, ring toss, spin-and-win, and pick-a-door, to name a few of the fun games and activities.

A mandatory “KidZone” waiver must be signed by a parent/guardian before game-tokens can be purchased.

This yummy event is free to enter and pits all chefs, bakers, and wannabe Food Network stars in the Pumpkin Dessert Contest.

10:00 a.m. – 11:00 a.m. – Drop off entries for judging

1:15 p.m. – Results Announced/Tastings Sold

All types of pumpkin desserts — pies, cakes, cookies, muffins, shortbreads, puddings, crisps, clafoutis, cobblers, tarts, candies, mousse, souffles, ice creams, tortes, trifles, creme caramels, flans, semi-freddos, crepes, strudels — are eligible but they must include fresh, frozen, or canned pumpkin.

Pumpkin pie spice alone does not count.

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 National Bank / Newcastle Chrysler Dodge Jeep

Entrants, who design, decorate and build the pumpkin racers, compete in three age groups:

Youth — 12 years and younger (Pumpkins decorated and raced by children, with parental assistance in building)

Teens — 13-19 (Pumpkins decorated and raced by teens, with or without parental assistance)

Adults — 20 years and up

The winners of each group face-off in the ultimate duel, a race to see who will be the Grand Champion and take home the checkered flag!

There also are prizes for scariest, funniest, and most creative pumpkin racers.

Official “Giant Pumpkin Parade”

Sponsor: Sullivan Tire & Auto Service

Music & Hooping by The Nikki Hunt Band

Commentary by John Riley & The Humble Farmer

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. Contestants are divided into two categories, aged 12 and under, and aged 13 and over, and a good time is had by all! Winners are awarded a T-shirt, all the pumpkin pie they can eat, and bragging rights for the next year!

Commentary by John Riley

Sponsors: Mid-Coast Energy Systems/Hannaford Supermarket & Pharmacy/Valley View Orchard Pies

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: Newcastle Chrysler Dodge Jeep / First National Bank

Entrants, who design, decorate and build the pumpkin racers, compete in three age groups:

Youth — 12 years and younger (Pumpkins decorated and raced by children, with parental assistance in building)

Teens — 13-19 (Pumpkins decorated and raced by teens, with or without parental assistance)

Adults — 20 years and up

The winners of each group face-off in the ultimate duel, a race to see who will be the Grand Champion and take home the checkered flag!

There also are prizes for scariest, funniest, and most creative pumpkin racers.

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, air-cannoned, dropped, trebucheted, or otherwise launched – so come see the gourds as they fly through the air.

Free to watch, $5 for 6 sling-shot shots.
There will be Live Music too!

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 the end.

KidsZone Sponsor: Tidewater Telecom

Queen’s Throne Sponsor: Phelps Architects

The KidsZone activities & events will be held on Columbus Day weekend (Saturday, Sunday and Monday) during Pumpkinfest, from 10:00 a.m. – 2:00 p.m. daily.

Families with children of all ages can enjoy the giant pumpkin bounce houses and the inflatable giant-slide, family photographs surrounded by Atlantic Giant Pumpkins & hay bales (think: “holiday cards” !!), temporary tattoos, face painting, sand treasures, pick-a-pumpkin, ring toss, spin-and-win, and pick-a-door, to name a few of the fun games and activities.

A mandatory “KidZone” waiver must be signed by a parent/guardian before game-tokens can be purchased.