The Most Underrated Towns In Connecticut
These underrated Connecticut towns helped build early America. One fought off a British fleet. Another opened the country's first law school. Guilford holds the oldest stone house in New England. Washington hides an abandoned railroad tunnel along the Shepaug River. The eight towns below carry centuries of colonial history and thousands of acres of open land between them.
Guilford
Guilford guards one of the most complete colonial centers in southern New England. Most people never make it past the shoreline. The Henry Whitfield State Museum dates to 1639. Reverend Henry Whitfield, the town's founder, built it from local stone. The interior still shows its original 17th-century architecture and period furnishings. Guilford rests on the Long Island Sound 24 minutes east of New Haven. The green has been the heart of town from the start. The third-largest collection of pre-Civil War homes in New England rings it. Cilantro Specialty Foods serves sandwiches and coffee nearby.
Chaffinch Island Park has picnic tables and grills with views of the Sound. A small jetty there draws summer swimmers. Jacobs Beach is the public swimming beach, with a snack bar and bathhouse. The Chittenden Park trailhead marks the southern end of the New England Trail. The route climbs north through Connecticut and Massachusetts. Grass Island lies across the marina, reachable on foot at low tide. Falkner Island Light flashes from a small island offshore. It is visible from the Guilford shoreline on clear days. Breakwater Books and the Village Chocolatier round out the walkable downtown.
Litchfield
Litchfield was home to the first law school in America. The town stays remarkably quiet about it. Tapping Reeve took on his brother-in-law Aaron Burr as his first student in 1774. He built a dedicated schoolhouse in 1784. It became the first proprietary law school in the United States. The school closed in 1833. By then it had trained more than 1,000 graduates. They included two future US vice presidents, Aaron Burr and John C. Calhoun, plus 28 senators and more than 100 members of the House. The Tapping Reeve House and Law School operates today as a National Historic Landmark. The original schoolhouse stands next to the Reeve residence. The town center wraps around the rectangular Litchfield Green in northwestern Connecticut.
The White Memorial Conservation Center lies just south of the green. It covers more than 4,000 acres with 35 miles of trails. The Little Pond Boardwalk Trail makes a 1.5-mile loop through Bantam River marshland. Litchfield Town Beach on Bantam Lake stays uncrowded most of the season. Mount Tom State Park is 10 minutes south. A stone observation tower marks the 1,325-foot summit. Kent Falls State Park is about 25 minutes west. A 250-foot waterfall drops along a paved viewing trail, with picnic areas and seasonal trout fishing.
New Canaan
New Canaan passes for a quiet commuter suburb until you reach the Philip Johnson Glass House in its woods. Johnson finished it in 1949 as his own residence. The 49-acre estate on Ponus Ridge Road includes the Glass House and 13 other structures he designed. The National Trust for Historic Preservation operates the site today. Guided tours run from May through November. Independent boutiques line Elm Street and Main Street downtown. The seasonal Spiga serves Italian food. The Roger Sherman Inn occupies a 1740 colonial home. Metro-North reaches New York City in just over an hour.
The New Canaan Nature Center covers 40 acres of meadows, woodlands, ponds, and marshes. It includes a maple sugar shed, a discovery center, and seasonal programming. Waveny Park covers 250 acres just south of downtown. The 1912 Waveny House at its center hosts community events all year. The New Canaan Museum and Historical Society rotates exhibitions on local history. Grace Farms spreads across 83 acres at the state border. Its SANAA-designed River Building was the first American commission for architects Kazuyo Sejima and Ryue Nishizawa. The building curves past a sanctuary, library, pavilion, and tea room.
New Hartford
A federally protected wild river runs straight through downtown New Hartford. That fact rarely leaves the valley. The Farmington River stretch here carries a Wild and Scenic designation. It protects the rapids and the surrounding watershed. Farmington River Tubing floats commercial trips through Class II rapids in the Satan's Kingdom area. The season runs from Memorial Day weekend through Labor Day. Main Stream Canoes and Kayaks rents boats for the calmer water downstream. The state-stocked Trout Management Area includes catch-and-release sections. They rate among the best fly-fishing waters in southern New England.
Lake McDonough covers 391 acres of reservoir. It has seasonal swimming beaches and a no-motor boating policy. The Barkhamsted Reservoir lies beyond it. It is the largest reservoir in the state and stays closed to the public. The perimeter roads still give scenic driving access. Collinsville Antiques Co. fills the former Collins Company axe factory, a National Historic Landmark. The space spans 100,000 square feet of mid-century and earlier finds. Ski Sundown opens winter lift service across 65 acres of trails south of downtown.
Norfolk
Norfolk puts on one of New England's oldest music festivals from its perch in the northwest hills. The Yale School of Music has hosted the Norfolk Chamber Music Festival at the Music Shed every summer since 1941. Students and professionals fill evenings on the Stoeckel Estate. The Infinity Music Hall books touring acts in an 1883 building. The 300-seat theater has a proscenium stage and an attached bistro. The town landed in the northwestern corner of Connecticut, where the Berkshire foothills cross the state line. Norfolk was incorporated in 1758. The Norfolk Historical Society Museum rotates exhibits inside the 1840 Old Town Hall. They cover the area's iron-furnace and dairy-farm past.
Haystack Mountain State Park rises just north of town. A 34-foot stone tower marks the summit. A half-mile climb reaches 360-degree views over the hills. Dennis Hill State Park covers 240 acres. The Dennis Pavilion crowns its summit, originally built as a private summer home in 1908. Campbell Falls State Park lies along the Massachusetts border. A 50-foot waterfall drops on the Whiting River. Wood Creek Pond lies northeast of town. It is one of the quietest paddling lakes in the state, with a public boat launch and a trout fishery.
Simsbury
Simsbury offers one of the only free bike-share programs in the country. Almost no one outside Hartford County knows. Rentable bikes wait at Simsbury Free Bike stations across town. The Farmington Canal Heritage Trail and the Iron Horse Boulevard route connect more than 80 miles of paved trail through Hartford County. The Old Drake Hill Flower Bridge crosses the Farmington River with a fully planted span. It started in 1892 as an iron-truss vehicle bridge. It now serves as a flower-lined pedestrian crossing.
Talcott Mountain State Park lines Simsbury's eastern border. The 165-foot Heublein Tower tops the summit. Gilbert Heublein completed it in 1914 as a summer residence. The summit looks out over the Farmington Valley. Sightlines reportedly reach into Massachusetts and New Hampshire on clear days. Stratton Brook State Park lies west of town and covers 148 acres. A red covered bridge crosses Stratton Brook. The park has Connecticut's first wheelchair-accessible swimming beach. Simsbury Meadows Performing Arts Center hosts the Hartford Symphony Orchestra's Talcott Mountain Music Festival each summer. Picnic seating spreads across the lawn. Plan B Burger Bar serves burgers, craft beers, and bourbons along Iron Horse Boulevard.
Stonington
Stonington still works for a living, which is why it never turned into a postcard. The fishing fleet docks at Stonington Town Dock. The borough occupies a narrow peninsula reaching into the Long Island Sound at the eastern end of the state. Water Street runs the length of the peninsula past independent shops, restaurants, and 18th-century houses. Dubois Beach has a small public swimming beach at the southern tip. A jetty there draws crabbers, with a view across the Sound toward Fishers Island. The Old Lighthouse Museum operates inside the 1840 granite lighthouse. Exhibits cover the War of 1812 Battle of Stonington and the local whaling and sealing trades.
The Captain Nathaniel B. Palmer House Museum preserves the 1853 home of a local sea captain. Palmer was among the first to sight the Antarctic Peninsula, at age 21 in 1820. Barn Island Wildlife Management Area covers 1,013 acres of coastal salt marsh and woodlot east of town. It opens for hiking, birdwatching, and waterfowl hunting in season. Saltwater Farm Vineyard occupies a restored 1930s airplane hangar on a 110-acre estate. It offers wine tastings, vine walks, and an upper-floor reception space. The Velvet Mill in nearby Pawcatuck houses an indoor farmers market, a brewery, a distillery, and rotating vendor stalls. The mill once made textiles.
Washington
Washington spreads across five separate villages. The whole town stays off the usual radar. They include Washington Depot, Washington Green, New Preston, Marble Dale, and Woodville. Each has its own historic district. The white-clapboard center along Washington Green gave Gilmore Girls its model for Stars Hollow, by wide belief. The Litchfield Hills setting helped. The Gunn Memorial Library and Museum works out of two adjacent buildings on the Washington Green. Rotating exhibits cover local history. Steep Rock Preserve covers 998 acres along the Shepaug River. The abandoned Shepaug Valley Railroad tunnel is one of the most-photographed spots on the 4.5-mile main loop.
Hidden Valley Preserve covers 728 acres of woodland north of downtown. A wooden suspension bridge crosses the Shepaug River. Paths run through old-growth hemlock stands. Hopkins Vineyard overlooks the north shore of Lake Waramaug. A hayloft room pours tastings above the lake. Lake Waramaug State Park covers 95 acres 10 minutes north, with a public beach. The Hickory Stick Bookshop in Washington Depot opened in 1951. It is one of the oldest continuously operating independent bookstores in Connecticut. Marty's Cafe and Eckert Fine Art share the building next door.
Connecticut's Best-Kept Towns
These eight towns never needed a spotlight to keep their history intact. New Canaan keeps Philip Johnson's Glass House out in its woods. Norfolk has hosted a summer music festival since 1941. Stonington still sends a fishing fleet out from its town dock every morning. Simsbury lends bikes for free along the Farmington River, where New Hartford floats tubers through Class II rapids. The colonial centers and the state forests stay open all year, and the people nearby treat them as part of the ordinary week.
