6 Fairy-Tale Small Towns In Connecticut
A bustling main street, white picket fences, town greens, and period homes. If that sounds like a movie set, take a trip to Connecticut to see the fairytale come to life. The storybook streets of New England are glorious all year round, but they are not just a lifeless backdrop. In these quaint towns, you will find rustic adventures, boutique shopping, historic sights, and much more. Take a trip to the northeast corner of the country to step back in time and enjoy a fairytale vacation.
Chester
Located in the scenic Connecticut River Valley, Chester is a lively small town with a picturesque Main Street. Settled in 1692, there is plenty of eye-catching architecture around town. Visit the Chester Museum at the Mill to browse two floors of exhibits about town and regional history while enjoying the beautiful setting of a historic 19th-century mill site. The museum is free and open on weekends from June to October.
If you are in the mood for homegrown entertainment, stop by the Chester Meeting House. Listed on the National Register of Historic Places, this community venue has been in continuous use for two centuries and is now the home of the Meeting House Players, who continue its legacy with a busy program of plays and performances.
When you have finished wandering, stop in at the Little House Brewing Company for refreshment. Housed in an historic building downtown that’s almost 200 years old, the brewery is a cozy tavern with an ever-changing tap list to suit any taste.
Sherman
A rural community at the northern end of Candlewood Lake, Sherman has an interesting connection with fairy tales. In the early 20th century, a resident named Perry Boney is said to have talked with fairies, earning himself the title of 'fairy seer.' Some stories even suggest Boney was a fairy himself.
You may not see any little people around town but Sherman is packed with magical sights and scenery including the 850 acre Deer Pond Farm Nature Reserve. This tranquil oasis contains 15 miles of hiking trails winding through classic Connecticut scenery of rolling hills, bubbling creeks, and flowery meadows. The reserve is open year-round, from dawn to dusk.
Visit the Old Store Gift Shop and Museum to shop as Sherman locals did 200 years ago. Built around 1802, the store was in continuous operation as a general store until 1998, when the Sherman Historical Society purchased the property and converted it into a museum and gift shop.
Sip locally-made, small batch wines among the New England countryside at White Silo Farm and Winery. This family-owned boutique winery is open for tastings from April to December and also hosts seasonal community events such as the Rhubarb Festival in early June, and Independence Day BBQ in July, and the Blackberry Festival in August.
Essex
The seaport village of Essex has a rich maritime history that’s evident in its historic buildings and attractions. The Connecticut River Museum tells the story of the town’s early history and resident mariners through interactive exhibits and displays, including two ships, a recreated 1614 Dutch yacht, and a research vessel. The museum is housed in the Connecticut River’s last steamboat warehouse, built in 1878.
For a closer look at the river, book a ride on the Essex Steam Train and Riverboat Tour. A two-hour round trip, the journey is a narrated train ride through the Connecticut River Valley followed by a cruise on a Mississippi-style riverboat.
Take a walk through the heart of downtown Essex and you will find one of the town’s most famous historical landmarks, the Griswold Inn. First established in 1776, this boutique hotel and restaurant is one of the country’s oldest inns, and it is still operating today. Across the road is the Inn’s charming gift shop, Goods and Curiosities, where you can pick up a souvenir from its range of eclectic and quirky New England-inspired merchandise, including books, art prints, crafts, foods, and jewelry.
Mystic
Mystic is as magical as its name suggests. A quaint seaport on the Connecticut coast, the town has a rich maritime history and beautiful heritage properties. Its fairytale look drew the attention of Hollywood producers in 1988 when the town became the picturesque backdrop to the classic 1988 Julia Roberts film, Mystic Pizza.
See Mystic’s seafaring past come alive at the Mystic Seaport Museum, a recreation of the original seaport village, complete with historic ships and cobblestone streets. Kids will also enjoy a visit to the Mystic Aquarium, where you can meet Beluga Whales and other magical marine residents.
Set sail and explore the coastline on a 19th-century schooner with Argia Mystic Cruises, a family-friendly adventure that takes guests out of the harbour and on a leisurely coastal cruise. The Argia sets sail from May to mid-October.
Madison
Madison is a pretty town in southern Connecticut, on the shores of the Long Island Sound. One of the most beautiful buildings in town is also one of the oldest. Built in 1785, the Allis-Bushnell House is listed on the National Historic Register. Open from May to October, the museum features displays on town history with exhibits including period furniture, ship models, paintings, clothing, children’s toys, and more.
As you wander around town, head towards the Scranton Memorial Gazebo to pick up the Madison Sculpture Mile, an outdoor art exhibit consisting of unique modern sculptures dotted around town.
A waterfront destination, Madison boasts three town beaches. You can also enjoy the scenic shoreline at Hammonasset Beach State Park which includes a two mile stretch of sandy beach, a tranquil nature preserve, and several walking trails with viewpoints over Long Island Sound and the Hammonasset salt marshes.
Kent
Just a short distance from the New York border, Kent is a rustic small town founded in 1739 on the banks of the Housatonic River. Known as the gateway to rural northwest Connecticut, this charming hamlet is particularly popular with hikers and nature lovers.
Kent Falls State Park is an otherworldly paradise where hikers can traverse a classic New England wooden bridge, climb a cascading 70ft waterfall, and enjoy a picnic among the beautiful forest foliage, which burns with autumnal color in the fall.
Back in town, get a feel for Kent through the centuries with a wander around the Flanders Historical District, where you can see sights including the Seven Hearths Museum. A pre-Revolutionary Home listed on the National Register of Historic Places, the 1751 building is now a museum with rotating art and history exhibits.
Take home a piece of history from The Company Store Antiques. The former company store of Kent Furnace operated in the 1800s, and the shop has a fascinating collection of furniture, folk art, homeware, paintings, accessories, and jewelry.
Small Town Charm in Fairytale Connecticut
Known as "the birthplace of America," New England has always been a special place steeped in history, heritage, and legend. Here, among the tranquility and beauty of the Connecticut countryside, you can almost believe in fairytales. Take a cruise on a 19th-century schooner, grab a bite in a 200-year-old tavern, visit a pre-Revolutionary home; the past is never far in this magical state, where its whimsical small towns offer a warm welcome.
