Seedling Sunday
May
18
9:00 AM09:00

Seedling Sunday

One tiny seed, harvested from a giant pumpkin, swaddled in soil, nurtured and loved, grows to form its pumpkin identity. This is your chance to raise a winner! 750 plantings will be displayed for adoption, care and nurture. A "celebrity" panel of professional giant pumpkin growers will be on hand to offer you formulas for raising formidable competitors, sometimes weighing up to 2,000 lbs. To ensure a perfect seedling sendoff, the Pumpkinfest Queen will be present to bless the tiny plants; and will be seated on her throne for fun family photos.

Let this four-month competition begin on Sunday, May 18th. This is a perfect family project, filled with education, fun, and wonder! Did you know that these pumpkins can grow as much as 25 lbs. in one day! Join in the fun! Your FREE seedling is waiting for you! See you on Sunday, May 18th!

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Pumpkin Deployment
Oct
9
3:45 PM15:45

Pumpkin Deployment

  • Damariscotta Pumpkinfest & Regatta (map)
  • Google Calendar ICS

  • A ballet of forklifts and giant gourds takes place every year on Thursday evening before the festival weekend to get the pumpkins into place all along Main Street in Damariscotta.

    Sponsor: Hammond Lumber

    Let us know if you would like to join the group of volunteers who help make this magic happen!

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Pumpkin Dessert Contest
Oct
11
10:00 AM10:00
Family, Kids, Saturday

Pumpkin Dessert Contest

  • Skidompha Public Library (Back Entry) (map)
  • Google Calendar ICS

  • Damariscotta Pumpkinfest & Regatta is pleased to invite all chefs, bakers, and wannabe Food Network stars to enter this year’s Pumpkin Dessert Contests. This yummy event will be held at Skidompha Library and samples will be for sale following judging.

    Please see www.mainepumpkinfest.com/dessert-contest for official rules for entry and other event details! oes here

    Sponsors: Barn Door Baking/Skidompha Library

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Pumpkin Derby
Oct
12
9:00 AM09:00

Pumpkin Derby

  • 18 Elm St Damariscotta, ME, 04543 United States (map)
  • Google Calendar ICS

The Pumpkin Derby brings yet another way to utilize a pumpkin, as spectators and contestants will enjoy the “soapbox-styled” pumpkin-car race! A perfect parental bonding opportunity!

Sponsors: Healthy Kids

Find the Derby Guidelines here.

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Pie Eating Contest
Oct
12
2:00 PM14:00

Pie Eating Contest

  • Elm Street Plaza Damariscotta, ME 04543 USA (map)
  • Google Calendar ICS

Participation will be first-come, first served for youth, adult and dogs! 🐶

See the Event page here for guidelines and registration forms.

Sponsors:

  • The Pie Eating Contest will be a spectacular involving races and feats of feasting taking place on Sunday at Elm Street Plaza. In between pie-eating, from about 4:30 onward, Team Maine Armwrestling will take the stage to bring delight to the audience with their amazing skills in demonstration.

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Pumpkinboat Regatta
Oct
12
4:00 PM16:00

Pumpkinboat Regatta

  • Damariscotta Municipal Parking Lot (map)
  • Google Calendar ICS

  • Described as the “extreme sport of gardening,” this real-life jack-in-the- beanstalk sport is an event you don’t want to miss! Spectators will be thrilled to watch giant gourds -steered by captains either paddling or powered by “wicked nice motors”- ply the waters of the Damariscotta River in a series of races.

    The Regatta will take place when high tide allows each year. For 2025, that will be at 4 PM on Sunday, October 12th! Needless to say, those 600 lb pumpkin boats need HIGH TIDE to be able to float & go really fast!

    The regatta can be viewed harbor-side, or via a “live feed” into The Lincoln Theater, where spectators are able to watch the event, seated in the warmth and comfort of the historic theater.

    Sponsors:

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Pumpkin Drop
Oct
13
11:00 AM11:00

Pumpkin Drop

The Drop is Back! After an absence of four long years, for many the best Pumpkinfest-event “The Pumpkin Drop” is returning to center stage! The pumpkins will be BIGGER! The drop will be HIGHER! The venue will be EXPANDED! The music will be AWESOME!  AND, the sights will be HILARIOUS!!!

Sponsors: Keeley Crane Service

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T-Shirt Contest Deadline
May
15
12:01 AM00:01

T-Shirt Contest Deadline

  • Damariscotta Pumpkinfest & Regatta (map)
  • Google Calendar ICS

Get those creative juices flowing and submit a winning design. A $500 prize will be awarded to the artist whose design is selected. And, fame and fortune will follow as the winning design will be featured on thousands of t-shirts and hoodies and seen by tens of thousands of happy visitors who come to celebrate the Damariscotta Pumpkinfest & Regatta on October 10-13, 2025.

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Buskers
Oct
14
11:00 AM11:00

Buskers

  • Damariscotta Pumpkinfest & Regatta (map)
  • Google Calendar ICS

Buskers, entertainers, sometimes known as street performers, are an added dimension of entertainment for Pumpkinfest, with each year bringing new specialties. See the lineup for the 2024 Buskers stage, located just off Main Street, at Elm Street Plaza.  We have a star lineup of performers for this year.

Sponsors: Main Street Grocery/First National Bank

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Food Court
Oct
14
8:00 AM08:00

Food Court

The “Food Court”, located at the Colby & Gale service station on Main Street, will be open Saturday, Sunday, and Monday. Participating in the Food Court this year will be Coastal Nutrition, Salty Boyz,  Lincoln Academy Class of 2026, Damariscotta Pumpkinfests famous cotton candy, RaggaeEats, Lincoln Academy Boosters, and the District 10 Masons.

Sponsors: Lafayette Hotels-Boothbay Harbor/Sandcastle Entertainment

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Food Court
Oct
13
11:00 AM11:00

Food Court

The “Food Court”, located at the Colby & Gale service station on Main Street, will be open Saturday, Sunday, and Monday. Participating in the Food Court this year will be Coastal Nutrition, Salty Boyz,  Lincoln Academy Class of 2026, Damariscotta Pumpkinfests famous cotton candy, RaggaeEats, Lincoln Academy Boosters, and the District 10 Masons.

Sponsors: Lafayette Hotels-Boothbay Harbor/Sandcastle Entertainment

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Buskers
Oct
13
10:00 AM10:00

Buskers

  • Damariscotta Pumpkinfest & Regatta (map)
  • Google Calendar ICS

Buskers, entertainers, sometimes known as street performers, are an added dimension of entertainment for Pumpkinfest, with each year bringing new specialties. See the lineup for the 2024 Buskers stage, located just off Main Street, at Elm Street Plaza.  We have a star lineup of performers for this year.

Sponsors: Main Street Grocery/First National Bank

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InfoZone
Oct
13
9:00 AM09:00

InfoZone

  • Damariscotta Pumpkinfest & Regatta (map)
  • Google Calendar ICS

The Damariscotta Chamber & Information Bureau will be located at the corner of Main Street and Theater Street to answer questions, and to hand out maps & other festival brochures. 

 

During the festival, local non-profits participate in InfoZone, also located on Theater Street.  InfoZone hours will be Saturday and Sunday, October 12-13 from 10 a.m. – 4 p.m.  

 

Visitors can learn about numerous non-profit organizations located in Maine’s midcoast, as the non-profits share information/brochures about the great work they do for so many in our community. 

Sponsors: Maritime Energy/Maritime Farms

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Food Court
Oct
12
11:00 AM11:00

Food Court

  • Colby & Gale Service Station (map)
  • Google Calendar ICS

The “Food Court”, located at the Colby & Gale service station on Main Street, will be open Saturday, Sunday, and Monday. Participating in the Food Court this year will be Coastal Nutrition, Salty Boyz,  Lincoln Academy Class of 2026, Damariscotta Pumpkinfests famous cotton candy, RaggaeEats, Lincoln Academy Boosters, and the District 10 Masons.

Sponsors: Lafayette Hotels-Boothbay Harbor/Sandcastle Entertainment

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Buskers
Oct
12
10:00 AM10:00

Buskers

  • Damariscotta Pumpkinfest & Regatta (map)
  • Google Calendar ICS

Buskers, entertainers, sometimes known as street performers, are an added dimension of entertainment for Pumpkinfest, with each year bringing new specialties. See the lineup for the 2024 Buskers stage, located just off Main Street, at Elm Street Plaza.  We have a star lineup of performers for this year.

Sponsors: Main Street Grocery/First National Bank

View Event →
InfoZone
Oct
12
9:00 AM09:00

InfoZone

  • Damariscotta Pumpkinfest & Regatta (map)
  • Google Calendar ICS

The Damariscotta Chamber & Information Bureau will be located at the corner of Main Street and Theater Street to answer questions, and to hand out maps & other festival brochures. 

 During the festival, local non-profits participate in InfoZone, also located on Theater Street.  InfoZone hours will be Saturday and Sunday, October 12-13 from 10 a.m. – 4 p.m.  

 Visitors can learn about numerous non-profit organizations located in Maine’s midcoast, as the non-profits share information/brochures about the great work they do for so many in our community. 

Sponsors: Maritime Energy/Maritime Farms

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Wawenock Golf Scramble
Oct
6
8:00 AM08:00

Wawenock Golf Scramble

Benefit for Wawenock Youth Programs

Sponsor: Wawenock Golf Club

  • Two-person best ball event (Gross Score)

    8:00 a.m. shotgun start (18 holes - open to the first 36 entrants)

    Fee: $75/person includes Gift Certificate, prizes, cart & awards

    Wawenock Golf Course, 685 State Route 129, Walpole

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