A Fairytale Town Hidden In The Connecticut River Valley Offers Art, Trails, And Authentic New England

Connecticut is full of undiscovered small towns off I-95 with beautifully preserved architecture, manicured town greens, and quaint downtown areas with independently owned shops and restaurants. East Haddam stands out among these for its deep connection to the arts, enviable setting on the Connecticut River, and network of nature trails. The town is steeped in authentic New England history, with iconic barns, hand-placed stone walls, and lovely 19th-century structures that give the town character in its historic district. 

Two immediately recognizable buildings visible from the river lend East Haddam a fairytale air and are both related to the arts. The 1877 Goodspeed Opera House is an elegant, one-of-a kind white Victorian building. It originally drew in audiences traveling via steamboat to the resort community of East Haddam. Down the river a bit and set high on a hill in an 184-acre state park, Gillette Castle was built to look like a medieval castle by the eccentric actor William Gillette in the early 1900s.

Another spot for outdoor recreation and trails in East Haddam is Devil's Hopyard State Park, whose ominous name comes from the indentations at the bottom of a waterfall that resemble devil's hoofprints. For more pristine nature, drive along state parks and forests in Connecticut's "Quiet Corner."

Time your visit to enjoy a performance at the Goodspeed Opera House, which has sent 21 shows to Broadway and won two Tony Awards for its contributions to the American musical art form. Three of the world's most famous musicals originated at the Goodspeed — "Annie," "Man of La Mancha," and "Shenandoah" — and stars like Ariana Grande and Idina Menzel performed here early in their careers. Next door, the Gelston House Restaurant and Inn offers prix-fixe meals for theatergoers, and guests can book a room to stay there from March through December.

A day in East Haddam wouldn't be complete without taking a tour of the 14,000-square-foot Gillette Castle to learn about its hidden stairwells and hear stories about its owner. William Gillette was an actor who wrote the first authorized Sherlock Holmes adaptation for the stage, came up with the catchphrase "Elementary, my dear fellow," and originated the character's deerstalker cap, curved pipe, and magnifying glass.

East Haddam is home to an artist residency program, I-Park, whose campus is occasionally open for visitors to walk the bucolic 450-acre grounds, attend an event, or see an art exhibition. Nearby, the Boardman House Bed and Breakfast has five luxurious rooms with amenities like a fireplace or private porch. Head to Higher Ground for coffee and decadent baked goods made fresh daily. Peruse the locally made art, jewelry, and other crafty gift items on display while supporting the local artisans.

Waterfall lovers and birders should head to the 860-acre Devil's Hopyard State Park and take the 0.4-mile trail to the 60-foot Chapman Falls, which passes through a covered bridge. Birders should be on the lookout for a variety of hawks, warblers, and flycatchers, among other species. At Gillette Castle, explore the grounds where you can walk along the wooded route of Gillette's now-defunct personal railroad. You can wander the park's trails and enjoy the picnic tables. From April to November, catch the Chester-Hadlyme ferry for a scenic excursion along the Connecticut River — it even takes cars.

From June through September, Cave Hill Resort welcomes guests in a camp-like atmosphere, offering stays in cabins or motel-style rooms, communal meals, and canoeing on the charmingly named Lake Mini HaHa. Strike up a game of volleyball, play a round of golf, try out the tennis and pickleball courts, or take a rowboat out on the lake and cast a line. This resort has been family-run for generations and also boasts a playground, swimming pool, paddle boats, and s'mores around a firepit. 

Nearby in Essex, you can stay and eat at America's oldest inn. If exploring other artsy New England towns is on your agenda, Northampton is a Massachusetts town with a vibrant downtown and Montclair, New Jersey, offers creative vibes and eclectic shops.