Few Connecticut areas better retain the look of yesteryear than the lower Connecticut River valley, particularly the neighboring Victorian villages of East Haddam and Chester. East Haddam (population 8,000) developed during the 19th-century steamboat era, and it still contains countless imposing Victorian structures, including the painstakingly restored Goodspeed Opera House, a magnificent four-story Second Empire building on the banks of the Connecticut River. The opera house boomed for its first few decades but fell on hard times by the middle of the 20th century and nearly faced the wrecking ball. Preservationists stepped in, and now the 360-seat Goodspeed shows three top-quality musicals annually.
Just downriver the curious Gillette Castle anchors the 184-acre slate park of the same name. Eccentric 19th-century thespian and Connecticut son William Gillette, famous for his Sherlock Holmes portrayals, labored live years to build the elaborate—some say bombastic—24-room fieldstone castle in 1919 for a thenastounding $1 million. When the actor died in 1937, he left his riverside property to be developed as a state park. You can tour the ambitiously restored bluff-top structure, or stroll along Gillette’s 3-mile-long mini-railroad. Trains no longer operate, but you can hike along the rail bed and admire the handsome stone rail station. Bring lunch— this is a wonderful place for a picnic and an afternoon spent exploring the area’s myriad nature trails.
Nearby Chester is a delightful spot for its shopping and dining. A smattering of art galleries fill the quaint, walkable downtown of this village perched along a section of the Connecticut River that the Nature Conservancy has culled one of “the last great places on earth.” Foodies laud the excellent Restaurant du Village, which occupies an unpretentious dining room that could easily pass for a country farmhouse in the South of France. The Mediterranean allusion continues when you choose from such signature pleasers as calamari sauteed with broccoli rabe and lemon vinaigrette, or hearty lamb shank braised with a red wine sauce and root vegetables. It’s wonderfully satisfying unfussy food, and the service is faultless, too.