Damariscotta Pumpkinfest and Regatta

Celebration of all things round and orange in Damariscotta this weekend

Special postmark available Saturday morning to commemorate 10th anniversary
Posted:  Monday, October 3, 2016 - 2:45pm

Pumpkinfest is just around the corner, and on Saturday morning, from 9:30 a.m. to noon at the Damariscotta Post Office at 173 Main Street, visitors can obtain a special postmark bearing a picture of a jack o’lantern (with an outboard motor!) with the legend, “Damariscotta Pumpkinfest and Regatta,” on any envelope or postcard with correct postage. The postmark is free. Patrons who want one but miss the hours at the post office can get one by mail.

Customers wishing to obtain a postmark should affix First-Class Mail postage to any envelope or postcard, address the envelope or postcard and tuck in the flap.  Place the envelope or postcard in a larger envelope and address it to Postmaster, followed by Damariscotta Post Office, 173 Main Street. Damariscotta, ME 04543.

Pumpkinfest is a three-day celebration of pumpkins large and small, and the events begin before the festival starts on Saturday. There will be shuttles from the Great Salt Bay School and Lincoln Academy to the festival from 8 a.m. to 6 p.m. Saturday, 7:30 a.m. - 6 p.m. Sunday, and 9 a.m. - 6 p.m. Monday. The shuttles don’t go to outlying areas, so leave time to get back to your car to get to events in other areas. The suggested donation is $1.

Pumpkins were weighed on Oct. 1 and 2, and once again, the adult winners for pumpkin were Charlie and Morningstar Lopresti of Buxton. This year, their pumpkin weighed 1,711.5 pounds. Local big-pumpkin growers included Richard Powell of Nobleboro whose pumpkin weighed 1,175.5 pounds, and Curt Crosby of Edgecomb. His weighed 1,155 pounds.

Justice Pierpont (no town given) came in first in the youth division at 1,233.5 pounds, Tanner Griffin of Harpswell, second, at 627.5 pounds, and Wesley Poole of South Bristol, third at 496 pounds.

On Thursday, Oct. 7, the giant pumpkins will travel Main Street on flatbed trucks and be lifted by forklifts and placed in position in front of businesses on Main Street. The “parade” begins at 3:30 p.m., and on Friday, Oct. 8, local Maine artists will decorate each of the 70-80 giant pumpkins lining Main Street in Damariscotta and Newcastle. Some will be painted, some will be carved, and all will be works of art.

Friday is also the day when the pumpkin boats for the Regatta will be carved and motors added. The public is welcome to come and carve their own or watch the boat builders, at Pinkham’s Plantation, 431 Biscay Road, in Damariscotta.


On Saturday, events really get under way. There will be kids’ events at Skidompha Library, including readings and crafts, from 10 to 11 a.m., and KidZone, including a pumpkin bounce house, games, face painting, and family photo opportunities will go on from 10 a.m. to 2 p.m. Saturday, Sunday and Monday. The fun takes place on Water Street.

The CLC YMCA will sponsor a fun run for kids and a zombie race for adults, beginning at 9:15 a.m. for kids and 9:30 for adults. Registration is from 8 a.m. to 9 a.m. at the YMCA.

A pumpkin dessert contest takes place from 10 a.m. - 2 p.m. in front of Skidompha Library, and there will be other street food, musicians and entertainers all along Main Street.

Kids, teens, and adults can build their own vehicle to race in the pumpkin derby, from noon to 4 p.m. at First National Bank on Saturday; the derby takes place in groups through the weekend.

At 2:15 p.m., the Giant Pumpkin Parade begins, with the Queen of the Pumpkins in attendance, on Main Street. Pumpkin pie-eating contests will begin immediately after the parade.

Evening events include Ken Axell, magician, illusionist, and mentalist, at Lincoln Theater at 7 p.m. with a suggested donation of $5, and Will and Doug at the Newcastle Publick House at 8 p.m., no cover charge.


The morning kicks off with a Pumpkin Pancake Breakfast at the Wells Hussey American Legion, Post 42, Ladies Auxiliary, at 527 upper Main Street, Damariscotta. The cost is $6 per person, and the breakfast runs from 7 — 11 a.m.

The Annual Pumpkin Derby will take place at 8:30 a.m. at the Elm Street Plaza – Weatherbird Hill.

From 10 a.m. - 1 p.m., the Damariscotta River Association will hold its pumpkin catapult and slingshot event at DRA’s Round Top Farm, 3 Round Top Lane. $5 for six slingshot pumpkins.

Boothbay Railway Village will hold its 49th annual Fall Foliage Festival on Route 27. Children under 12 and members are free; adults are $4, and train rides are $5.

The Pumpkinboat Regatta will be held at 3 p.m., both at the harbor and live-fed into Lincoln Theater, with concerts by Hollowbody Electric Band at 12 noon and 4 p.m., and commentary by Larry Sidelinger and Don Carrigan.

The Horseshoe Crabs will play at Schooner Landing Restaurant from 4-7 p.m. No cover charge.


There will be a free kids’ morning movie, ‘The Lego Movie’, at Lincoln Theater at 10 a.m., and more kids’ fun at the KidZone from 10 a.m. - 2 p.m.

From 11 a.m. to 2 p.m., the Damariscotta River Association will hold its pumpkin catapult and slingshot event at DRA’s Round Top Farm, 3 Round Top Lane. $5 for 6 slingshot pumpkins.

The afternoon winds up with the kids’ pumpkin hunt and 180-foot pumpkin drop at the DRA’s Round Top Farm. Music by The Nikki Hunt Band begins at 1 p.m., and kids register for the pumpkin hunt from 1:30 to 2:15 p.m. The hunt begins at 2:30 p.m., immediately followed by the pumpkin drop.