T-Shirt Contest Deadline
May
14
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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Seedling Sunday
May
17
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
8
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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Artists at Work
Oct
9
to Oct 10

Artists at Work

  • Main Street Damariscotta, ME United States (map)
  • Google Calendar ICS

  • Witness artists transform giant pumpkins into amazing works of art! Artists will be working all day on Main Street paint, carving, and decorating their pumpkins.

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Pumpkin Dessert Contest
Oct
10
10:00 AM10:00

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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Buskers
Oct
10
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 2026 Buskers stage, located just off Main Street, at Elm Street Plaza.  We have a star lineup of performers for this year.

Sponsors:

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Food Court
Oct
10
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 and Food Trucks in the back parking lot, will be open Saturday, Sunday, and Monday. Stay tuned to see who will be participating in the Food Court this year.

Sponsors:

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Pumpkin Derby
Oct
11
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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Buskers
Oct
11
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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Food Court
Oct
11
11:00 AM11:00

Food Court

The “Food Court”, located at the Colby & Gale service station on Main Street and Food Trucks in the back parking lot, will be open Saturday, Sunday, and Monday. Stay tuned to see who will be participating in the Food Court this year.

Sponsors:

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Pumpkinboat Regatta
Oct
11
12:00 PM12:00

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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Pie Eating Contest
Oct
11
3:00 PM15:00

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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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 2026 Buskers stage, located just off Main Street, at Elm Street Plaza.  We have a star lineup of performers for this year.

Sponsors:

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Food Court
Oct
12
11:00 AM11:00

Food Court

The “Food Court”, located at the Colby & Gale service station on Main Street and Food Trucks in the back parking lot, will be open Saturday, Sunday, and Monday. Stay tuned to see who will be participating in the Food Court this year.

Sponsors:

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Coastal Kids Preschool welcomes Carl the Collector for a Sensory-Friendly Event!
Oct
12
11:00 AM11:00

Coastal Kids Preschool welcomes Carl the Collector for a Sensory-Friendly Event!

Sensory-Friendly Events Provide Families:

  • Accessibility–Allowing individuals with sensory sensitivities to participate in events without feeling overwhelmed.

  • Well-being–A safe space for children/families to decompress and regulate when needed.

  • Inclusion–Promoting an environment where everyone is welcome.

Visitors at the Coastal Kids Preschool event can expect a sensory-friendly pumpkin drop, pumpkin decorating, dedicated sensory spaces, activities

Accessible Parking Available at Coastal Kids Preschool

All others may access Coastal Kids Preschool via the Nature Trail from the CLC YMCA or by Pumpkinfest Bus

Find out more: www.CoastalKidsMe.org/Pumpkinfest

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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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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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