8 Fairy-Tale Small Towns In New England

Magic, royalty, and enchantment are just a few things that come to mind when you think of fairy tales. But what if you could find that type of charm in small towns and not just on big screens. An enchanted forest could be a marshland located along a seashore, a magical spell could be a feeling you get after visiting a quaint landmark, and sense of royalty can be how you feel after slipping into a modern-day castle for a tour. These fantasy ideas come to life and more in these eight small fairy tale towns in New England.

Kennebunkport, Maine

Kennebunkport is an appealing coastal town in Maine that is famous for their sandy beaches, small town charm, historic downtown, and of course the lobster rolls. One of two public beaches, Goose Rocks Beach is three miles of blissful shoreline, protected by the Goose Rocks barrier, making swimming more relaxing. Swim, tan, kayak or paddleboard in the waves of Goose Rocks Beach for an unforgettable day in the sun. Stick to the coastline and visit the Goat Island Lighthouse. Established in 1833 and renovated in 2011, this historical landmark encourages guests to visit by boat or view the lighthouse from the Cape Porpoise pier landing. The residence is private, but the lighthouse keepers have been graciously providing tours to eager patrons.

A visit to the coast isn’t complete without a famous lobster roll. You can’t get much fresher than with lobster straight from the Atlantic Ocean. Since 1953 Mabel’s Lobster Claw has been dishing up classic Maine seafood. A vibrant coastal village, Mabel’s atmosphere matches Kennebunkport’s culture and spirit. Located on Ocean Avenue residents and tourists have been venturing to the establishment for the typical seafood fare, including lobster rolls, fried clams, and steamed lobster.

Bar Harbor, Maine

Another widely popular Maine destination is the unique town of Bar Harbor. The town itself is located on Mount Desert Island and accessible by road, ferry or airliner. One of the state’s largest attractions is found in Bar Harbor: Acadia National Park. With multiple trails overlooking either the mountains or the ocean the park is full of endless views. With nearly 4 million visitors a year Acadia is one of the top ten most visited national parks in the US. Drive or hike up to the highest point on the eastern seaboard of the US with a trip up Cadillac Mountain.

A museum that was originally part of the national park, is now located in the heart of downtown. The Abbe Museum features the history and culture of Wabanaki. The museum’s exhibits are currently updating as well as their special events and workshops. With everchanging exhibits there is always something new to learn and explore. Being coastal, since it is an island and all, Bar Harbor is also a significant location for a fresh classic lobster roll. In 2019 a vacation to Maine led to a wild dream, that turned into a restaurant for the owners. Originally from Florida, the owners brought their own flair to the “run down” lobster pound and made it their own. Enjoy all that Bar Harbor Lobster Pound has to offer including fresh lobster right off the dock.

Block Island, Rhode Island

Located just 12 miles off the coast of Rhode Island is one of their smaller towns. The 11-square-mile island is only accessible by boat or small commercial airliner and looks like something right out of a fairy tale novel. Block Island has 15 uniquely different and beautiful beaches for visitors to enjoy. The most popular amongst tourists is arguably Ballard’s Beach on Water Street. With an oceanfront restaurant serving cocktails and food, and VIP cabanas available beachcombers can settle in for a fun filled day in the sun.

Visitors can bring cars over by ferry, but if you find yourself there without a car, jaunt around the island on a Moped from one of five rental shops on the island. Make sure to scoot over to Painted Rock to leave your own memento that you were there. Residents and tourist have been painting the rock with their own messages and pictures since 1962 and today it has grown into such a popular tradition there could be multiple images painted on the rock in one day by multiple parties. End your day on the island with a night at the Block Island Beach House, the only hotel on the island to offer beachfront hotel rooms. Built in 1873, the hotel includes a three-story section with a dome that was completed in 1884 that forms the central part of the current hotel, and a four-story building was added on the left-hand side in 1888.

Nantucket, Massachusetts

Part of the state of Massachusetts, the island of Nantucket holds its own allure that brings tourists back year after year. Enjoy a view of the island from the top of the Sankaty Head Lighthouse. A beloved island icon, the lighthouse was erected in 1849 and stands at 158 feet above sea level. Erosion caused the lighthouse to be required to be moved further inland, where it sits till this day, and visitors are encouraged to visit the grounds and the top of the lighthouse when tours are in season.

Another iconic island lighthouse can be found in the Great Point Coskata-Coatue Wildlife Refuge. Protruding from the tip of the island, Great Point is an undeveloped barrier beach that houses the iconic Great Point Lighthouse. Featuring views of the ocean, maritime oak forests, and rolling red cedar savannah, the refuge is a high point for naturalists, anglers, and bird watchers. Another favorite focal point of the refuge is the great opportunity for Grey Seals spotting. For a final spot to enjoy relaxation and a little bit of wanderlust, cool down in the ocean waters at Surfside Beach. One of the more popular beaches on Nantucket, Surfside is a wide flat beach with rolling surf over sandbars. Surfers will frequent the beach to catch the best waves, but it is also widespread for volleyball, boogie boarding, and sunbathing.

Woodstock, New Hampshire

The charming town of Woodstock features tranquil sites to enjoy the sights and sounds of the region. For mythical fun in the region, visit Sculptured Sand. Follow a winding path through a dark forest to view more than 25 fairy tale scenes created entirely out of sand. Set against the backdrop of the White Mountains, the exhibit features characters from "Alice in Wonderland," "Cinderella," "Aladdin," and more. Another attraction in Woodstock that looks like it was plucked straight out of a fantasy movie is the Lost River Gorge and Boulder Caves. Follow the wooden boardwalk as it winds through the gorge and takes adventurers along the Lost River, by rock walls and massive boulders, and around boulder caves until finally making it to the cascading waterfalls.

For an extra daring thrill follow the Forest Adventure Trail to the suspension bridge. And what’s a fairy tale without castles? During the winter season visit the New Hampshire Ice Castles. Ice caves, frozen mazes, and tunnels are just part of the enchantment of these immense structures. Illuminated with the glow of winter the castles offer opportunities for sleigh rides, ice slides, a mystic forest light walk and so much more.

Woodstock, Vermont

Not to be confused with town of the same name in New Hampshire, Woodstock, Vermont has its own attractions and picturesque views to enjoy. In 1836 construction of the Taftsville Covered Bridge was completed, making it one of the oldest covered bridges in the state as well as the US. Spanning the Ottauquechee River, it is the second longest bridge in Vermont at 189 feet in length. Take a stroll across the timeless bridge on foot or by car and enjoy the rushing waters below. For more New England classic views, hike to the top of Mount Tom. The peak of the mountain reaches 1,357 feet and is located in the middle of town. Four main entrances lead to trails that twist along the entirety of the mountain. Faulkner Trail will take hikers directly to the summit of Mount Tom.

For a final local experience spend some time at Sugarbush Farm. The 500-acre farm offers free samples of cheese and maple syrup and includes a farm store complete with locally made jams, mustards, spreads, and meats. Although the maple syrup is made in the Spring, visitors can partake in a self-tour to see the maple woods where it is made.

Mystic

Imagine a pizza place that is so beloved it inspires an entire movie. Mystic Pizza, the local pizza joint, was the inspiration behind the movie of the same name. In 1988 the movie was released centering around the lives of three young waitresses and after its release the small pizza place could hardly keep up with the demand of visitors coming to view the latest Hollywood icon. Stop by one of their now two locations to enjoy a slice of heaven. Step away from the Hollywood buzz and head out on a seaside voyage with an excursion through Sail Away Argia. This vintage vessel is the last commercial sailing ship in the town of Mystic and takes its passengers on daytime and sunset cruises.

For one last outdoor excursion find some time to visit Denison Pequotsepos Nature Center. Immerse yourself in forest, wetland and meadow displays depicting Connecticut’s diverse habitats and wildlife. Hike the trails and come across rehabilitated hawks and owls, native to southern New England, in outdoor flight enclosures. Search for frogs, fish, turtles and snakes, centipedes, ants and mushrooms in the Life Under a Log exhibit, and enjoy other displays featuring birds, eggs, nests and skulls.

Newburyport, Massachusetts

Enjoy plenty of waterfront activity in Newburyport with a cruise through the excursionists at Newburyport Whale Watch. The 106-foot cruise liner takes passengers down the Merrimack River out to the Gulf of Maine to the whale feeding grounds. Keep your eyes open for Humpback, Finback, and Minke Whales in addition to Porpoise, Seals, Sharks and an array of Sea Birds. Back on land, stroll through the Newburyport Waterfront Park. The park has a boardwalk running along the Merrimack River with ample opportunities for viewing all the water activity. The park also hosts a plethora of events from local theater performances to the Riverfront Music Festival.

For beautiful scenic views of 19th century gardens and plants, rolling meadows, lofty pines, and one of the largest naturally occurring nestle of mountain shrubbery in the state, hike or bike through Maudslay State Park. Sixteen miles of trails take visitors through fields, forests and other scenic areas. If you happen to visit in late spring relish in the bloom cycle that begins with flowering trees, then progresses into the mid and late blooming varieties of rhododendrons and azaleas.

When some people think of fairy tales, colossal castles, mystical forests, mythical creatures, or alluring seascapes come to mind. In one way or another these sites can be found in any of the New England states. Meander through deep gorges, hike to cascading waterfalls, and witness larger than life animals in their natural habitat. There is no shortage of adventure or magic in these eight small fairy tale towns in New England.