10 Of The Most Eccentric Towns In Maine

Maine welcomes visitors who want to relax on gorgeous beaches and discover the hidden oddities of its charming coast. The state is popular in media, especially media that surprises audiences by balancing the state's natural serenity with its perfect opposite: horror. Here, Stephen King imagines dark deities to contrast the bright and calm coast, while Jessica Fletcher in Murder, She Wrote spends her days riding her bike on gentle paths between crime scenes. The state may not be scary, but it is certainly eccentric. The towns on this list are full of surprises and wonders that will feed your imagination and soul in equal measure.

Vinalhaven

This island town has so much to offer, starting with gray seals lining the shore at Seal Bay. Wildlife is abundant here, where the pristine landscape has been preserved and protected, keeping it a wild escape for humans and a haven for animals. Release your inner aquatic animal at Lawson Quarry Pond, a locally loved swimming hole where sun-warmed stones lead to crystal spring waters.

Those who don’t want to swim in the spring water can lie upon the flat rocks in the sun or in the shade of the pine trees and drift off to the sound of birdsong in the distance. After appreciating this town's wild side, discover its roots at the Vinalhaven Historical Society Museum. This small but mighty museum houses photographic and genealogical records, as well as historic tools used in ancient industries like fishing and farming.

Lubec

Being the easternmost town in the contiguous US, Lubec makes up the north region of The Bold Coast, which has trails that wind all the way up to Canada. The bountiful nature here creates many stunning hikes through forested trails, coastline, and vertical cliffs. Travelers walking the coastline will soon find the West Quoddy Head Lighthouse. The lighthouse is easy to spot due to the candy-cane stripes that give it a vintage feel. For more stunning sightseeing, head to the Roosevelt International Bridge, which not only offers magnificent views but also the chance to visit Canada. The bridge connects to Campobello Island, a tiny land formation that seems to have drifted in from a fairytale. To access this little island, you only need stamina to cross the bridge and a passport to pass border patrol.

Belfast

Walking through downtown will immerse visitors in the artistic heart of this small town at Belfast Art Walk. On the fourth Friday of each summer month, eight galleries open their doors, creating one long street of open portals to mini-universes made from vibrant colors in different mediums. After venturing downtown, grab some farm-fresh produce and baked goods at Chase's Daily. This vegetarian market restaurant hybrid is locally beloved for its eccentricity (they only serve dinner once a week, you will never find meat on their menu, and there is no hierarchy in their business model) and sustainability, which makes it so rare. To get the best view of this small town, take a train ride with the Belfast & Moosewood Lake Railroad. Weekend round-trip packages offer delicious food, comfortable accommodation, and a beautiful view of Belfast and beyond out of the rattling train windows.

Monhegan Island

Monhegan Island is a rocky island that stretches ten miles across the Gulf of Maine. While it is only accessible via boat and mainly used as a “walking Island”, these rocky shores are also home to artist studios and galleries. Monhegan Museum of Art & History showcases art exhibits as well as information on the Second World War, which profoundly affected Monhegan Island.

Take a walk along the rocky cliffs that lead to the lighthouse. Built in 1850, this historic stone structure is beautiful to behold; its light cutting through the sea mist adds to the storybook atmosphere. A short walk away, visitors will find Monhegan Brewing Company, a small family-owned and operated brewery. An on-site food truck serves seafood that pairs perfectly with their brew.

Eastport

This town knows how to party, usually with a nautical theme. The Mermaid Parade and the Eastport Pirate Festival bring out the most playful side of locals and tourists, who gather in costume to sing sea shanties and perform with swords, flame, and more. Lean even more into the aquatic themes by taking a boat tour in Passamaquoddy Bay, where passengers can see whales and dolphins breach the water.

Serving as a “cultural anchor and cultural catalyst”, The Tides Institute & Museum of Art is where to go if you are curious about local arts and cross-border culture. The museum connects Eastport to the rest of the world through colorful canvases and artistic collections.

Wiscasset

Are you really in Maine if you don’t try a lobster roll? The legendary Red’s Eats may have the best in all of New England. The caboose-shaped restaurant sits on the Sheepscot River, creating a dreamy and idyllic view to accompany Maine’s famous lobster. With a full stomach and a curious mind, wander through Wiscasset Antiques Mall. Here, strange and rare antiques await those who want to discover new pieces of the old world. Explore another time capsule at Castle Tucker, an eccentric 1800s mansion still filled with original furnishings.

Hallowell

Hallowell is known for being a little city with a big heart. Dive into this big heart by browsing the funky vintage shops and antique stores on Water Street. The Rusticators Emporium is especially beloved for its offbeat collection of eclectic goods and antiques. Multiple vendors sell within the Emporium, creating a wide range of goods and a lot of history.

Listen to live music at The Quarry Tap Room to feel the local vibrations. Known as a “modern day saloon”, this is a great spot to talk with locals and dance with them. More fun awaits at the annual Old Hallowell Day, a town-wide party with art, music, tournaments, baked goods, and a parade.

Brooklin

While walking along the waterfront of this beautiful town, visit the Brooklin Boat Yard. Here you can marvel at the traditional craftsmanship of vintage boats being renovated. Travelers can also see new designs and watch them as they take them to the sea. After witnessing the amazing woodwork found at the boat yard, try the art yourself at the Wooden Boat School. The school offers courses in woodworking as well as seamanship and sea-related crafts. For more beautiful views, head to Harriman Point. Walk along this coastal beach with colorful shells beneath your feet and amazing views of Mount Desert Island and Blue Hill Bay surrounding you.

Stonington

The town of Stonington rests on the south side of Deer Isle Island. While it is wonderfully eclectic in its own right, the town is only a ferry ride away from what feels like another universe. Isle au Haut is a wild, forested rocky island full of streams and rapids. This seemingly otherworldly realm is excellent for long walks, fishing, and swimming. Back on the mainland, see a performance at Opera House Arts, a historic theater that mixes classics, avant-garde, and even puppetry.

The variety of shows is suitable for all ages, making this a great destination for traveling families. After the show, venture through 98 acres of dense forest stretches along Stonington at Crockett Cove Woods Preserve. Here, rolling mossy hills offer tranquility and peace throughout multiple trails cutting through tall spruce trees.

Rangeley

Wildlife lovers will find their haven in Rangeley, where travelers can spot moose on a guided moose tour near Rangeley Lakes. These majestic beasts are usually seen in the early morning during late spring to mid-summer. To get a better view of this town, climb Saddleback Mountain. “Maine’s favorite mountain” is known for its slopes, but it is also a great place to take off the skis and enjoy a walk through the snow or rent a mountain bike to ride through the rocky paths of the mountain. Rangeley Lakes Trail Center is another great option for those seeking the tranquility of snow-topped mountains. Offering 50 KM of recreational trails, Rangeley’s is known for its Nordic skiing, hiking, and snowshoeing opportunities.

Maine feels like a dream that leaked into reality through spring water and rocky islands. This coastal state sets the stage for performance art, craftsmanship, outdoor sports, and the ultimate relaxation. Adventurers of all kinds can find their perfect match within these small towns. Whether you want to swim in Vinalhaven’s natural spring water, climb snowy mountains in Rangeley, or drink a brew and walk through art galleries on Monhegan Island, this list will help you create your most eccentric travels in 2025.