People race giant hollowed pumpkins across this Maine harbor every October

Maine’s Twin Villages hold more than you’d expect

Damariscotta sits on a tidal river in Midcoast Maine, about an hour north of Portland, and most people drive right past it on their way somewhere else. That’s their loss.

This town of roughly 2,300 people has been surprising visitors since the 1800s, and it still does.

The oysters are some of the best in the country, the history runs deep, and once a year in October, people race hollowed-out pumpkins across the harbor. You’ll want to stay longer than you planned.

A town built from the river and the sea

Damariscotta takes its name from the Algonquian word Madamescontee, meaning place of many alewives.

Those small, salty fish still run up into Damariscotta Lake each spring, just as they did when the Wawenock Abenaki people lived along this river for thousands of years.

Europeans arrived around 1640, settling upriver from Pemaquid.

The town was officially incorporated on March 15, 1848, and it grew fast, with shipyards launching clipper ships and local brickyards supplying the bricks that built Boston’s Back Bay neighborhood.

The Damariscotta River grows 80 percent of Maine’s oysters

Cold, salty water moves through this river in a way that does something special to oysters. The flavor comes out clean and briny, and the region gets compared to Napa Valley for what it produces.

The Damariscotta River turns out about 80 percent of all farmed oysters in Maine, a tradition that took its modern form when Pemaquid Oyster Company started up in 1986.

You can get out on the water by boat or kayak and tour the working farms where it all happens.

Native Americans left 30 feet of shells behind

Just north of town, a short trail leads to one of the oldest oyster bars in North America.

The Whaleback Shell Midden is a state historic site where Native Americans piled oyster shells over centuries, building the mound between 2,200 and 1,000 years ago.

The original pile ran 1,650 feet long and reached more than 30 feet deep. In the late 1880s, most of it got hauled away to make chicken feed.

What remains sits above the river quietly, with the water in view and almost no one else around.

Main Street still looks like 1880

You can walk the length of Damariscotta’s Main Street in 15 minutes and count Federal, Greek Revival, and Italianate buildings all in a row.

The old seaport storefronts now hold small galleries and shops, and the grand homes of sea captains from the shipbuilding era still stand along the side streets, solid and unaltered.

The Damariscotta River Walk runs along the harbor if you want to stretch your legs past the buildings and get closer to the water.

Lincoln Theater has been running since 1876

Lincoln Theater opened as Lincoln Hall on Jan. 26, 1876, and it marked its 150th anniversary in early 2026. Walk inside and look up.

Two original chandeliers from the 1876 building are still hanging where they’ve always been. The theater now puts on about 500 events a year, from films to concerts to plays and community gatherings.

It has never really stopped being the center of town life. In a place this small, 500 events a year means something is always going on.

The 1754 Chapman-Hall House is the oldest in town

Nathaniel Chapman, a housewright from Ipswich, Massachusetts, built this house in 1754, and it has stood through everything since. The Chapman family held it until 1835, then the Hall family kept it until 1907.

By 1960, it was close to coming down before locals pushed back and saved it.

Walk through the first floor today and each room is set up for a different era: 1754, 1790, and 1820. You move from one century to the next in three steps.

Skidompha Library’s name is actually an acronym

The Skidompha Library Association incorporated on March 13, 1905, with 1,476 donated books above a grocery store on Main Street. SKIDOMPHA is an acronym built from the surnames of the founding members.

The library now serves Damariscotta, Newcastle, and Nobleboro, and in 2005, it received the National Medal for Museum and Library Service at the White House.

For a small-town library that started above a grocery store, that’s a long way to travel.

Giant pumpkin boats race across the harbor in October

Local resident Buzz Pinkham captained the first pumpkin boat in 2005. By 2007, he and Billy Clark had turned it into an official town festival.

Each October, racers lower themselves into hollowed-out pumpkins weighing 400 to 700 pounds and paddle across the harbor.

Between 10,000 and 15,000 people show up, and along with the race, you get a giant pumpkin contest, a parade, a pumpkin derby, and decorated pumpkins lining every inch of Main Street.

It is exactly as ridiculous as it sounds, and completely worth it.

Great Salt Bay hosts one of the oldest animals on Earth

The Damariscotta River empties into Great Salt Bay, the first marine protected area in Maine. The bay sits at one of the northernmost points in North America where horseshoe crabs still come to spawn.

These animals have existed in their current form for more than 250 million years, and Maine has banned taking or possessing them since 2003. You won’t find crowds here.

The bay is quiet, the water moves slowly, and what surfaces along the shore has been doing so since before the dinosaurs.

Pemaquid Point Lighthouse sits 25 minutes south of town

Drive south about 25 minutes into Bristol and you reach Pemaquid Point Lighthouse, the one pictured on the Maine state quarter.

The first tower went up in 1827, but poor construction brought it down and a stronger one replaced it in 1835. From Memorial Day through Columbus Day, you can climb the 38-foot tower.

A storm hit the historic bell house in January 2024, but crews restored it fully within months. Stand at the point and the Atlantic opens up in three directions.

Kayak past working oyster farms and spot seals on the way

Narrated boat cruises run daily on the river through the warm months, and guided kayak tours wind past working oyster farms and into quiet coves.

Seals, herons, and ospreys show up regularly along the banks. On some tours, you paddle out to a farm, stop, and shuck oysters right there on the water.

If you’ve never paddled before, the Damariscotta River is a good place to start. The water stays calm, the scenery moves slowly, and lunch is already built into the route.

Visit Damariscotta, Maine

To get out on the river and taste oysters straight from the farm, Damariscotta is about an hour north of Portland on Maine’s Midcoast.

Most of what you’ll want to see sits within a walkable stretch of Main Street and the waterfront.

The Damariscotta Region Information Center at 276 Main St. can point you toward boat tours, kayak outfitters, historic sites, and local farms. Stop in before you start exploring.

The staff knows the area well and the town rewards a slow pace.

This article was created with AI assistance and human editing.

Read more from this brand:

• Bath: the small Maine town that outbuilt the Japanese Empire in WWII
• The wild Maine island that Thomas Edison’s son refused to let die
• Where to find Maine’s abandoned island town couldn’t find enough voters to keep existing