8 Coolest Small Towns in Connecticut for a Summer Vacation

By Memorial Day, the Essex Steam Train is back on the Connecticut River with its connecting riverboat run. By Independence Day, Madison's Hammonasset Beach State Park has hit its peak day-use traffic of about a million summer visitors, the busiest state park in Connecticut. By Labor Day, Old Lyme's Roger Tory Peterson Estuary Center runs its Swallow Cruise to watch half a million tree swallows roost in the Great Island marsh at dusk. Eight Connecticut towns run the summer calendar in their own ways.

Essex

Essex sits on a peninsula where the Connecticut River widens before emptying into Long Island Sound, six miles north of the river's mouth. The Connecticut River Museum at Steamboat Dock holds the world's first combat submarine (a 1775 replica of David Bushnell's Turtle, used in the American Revolution) and rotating exhibits on the river's shipbuilding history. The Griswold Inn on Main Street, opened in 1776, is one of the oldest continuously operated taverns in the United States and still serves a Sunday Hunt Breakfast in the wood-paneled tap room.

The Essex Steam Train & Riverboat runs the longest continuously operating steam railroad in the country, a 1920s-era train pulled by a coal-fired locomotive that connects to a riverboat for a combined two-and-a-half-hour run up the Connecticut River. The Thomas the Tank Engine weekends in June pack the depot with families. Essex was the only Connecticut town attacked by the British during the War of 1812, in a 1814 raid that burned 28 American ships; the town still marks the date with a "Loser's Day" parade.

Glastonbury

Glastonbury (population about 35,000) stretches nine miles along the east bank of the Connecticut River, directly across from Hartford. The Rocky Hill-Glastonbury Ferry, in continuous operation since 1655, is the oldest continuously operated ferry service in the United States; the four-minute crossing on the Hollister III runs daily from May 1 through October 31 and costs $5 per car. The town was named after Glastonbury in Somerset, England, where Joseph of Arimathea is said to have planted his staff.

The Audubon Center at Glastonbury and the trails of Riverfront Park anchor the outdoor calendar. The Summer Concert Series in Riverfront Park runs every Wednesday evening from late June through August, free and open to all. Apple Harvest Festival each October takes over the town green with cider, pies, and craft vendors. Two strong year-round draws are the Connecticut Audubon Society's Glastonbury Sanctuary and Wickham Park, a 280-acre former private estate now operating as a public park with English gardens and an oriental garden.

Madison

Madison runs along Long Island Sound between Branford and Clinton and holds Hammonasset Beach State Park, the largest shoreline park in Connecticut at 919 acres with more than two miles of beach. The Meigs Point Nature Center inside the park runs free interpretive programs through the summer, including the Saltwater Touch Tank for kids and birding walks led by state-park staff. Hammonasset draws around one million visitors a year, making it the most-visited state park in Connecticut.

Downtown Madison runs along Boston Post Road with R.J. Julia Booksellers (a 1990 independent that hosts hundreds of author events a year, anchored by the long-running Booklovers Bus) and the Madison Art Cinemas, a 1912 movie house restored for first-run independent films. The Shoreline Greenway Trail is a coastal route in development that already connects sections through Madison, Branford, and Guilford.

Mystic

Mystic is a village split between the towns of Stonington and Groton at the head of the Mystic River, with a year-round population of about 4,200. Mystic Seaport Museum on the river's east bank is the largest maritime museum in the United States by acreage, with a recreated 19th-century coastal village and the Charles W. Morgan, the last wooden whaleship in the world (built 1841, a National Historic Landmark, fully restored in 2014). The neighboring Mystic Aquarium is one of only a few US aquariums permitted to house beluga whales and runs the Sea Research Foundation.

The 1988 Julia Roberts film Mystic Pizza was shot in and around the village; the real Mystic Pizza restaurant at 56 West Main Street is still open and still slings pizza, though its current decor leans heavily on the movie connection. The Mystic River Bascule Bridge in the middle of the village raises every 40 minutes from 7:40 AM to 6:40 PM in summer; locals time their walks down Main Street around it.

Old Lyme

Old Lyme is where American Impressionism set up shop. From about 1899 to 1937, painters including Childe Hassam, Henry Ward Ranger, and Willard Metcalf boarded with Florence Griswold at her Georgian mansion on Lyme Street, paying their rent in canvases that they painted directly onto the dining-room and parlor panels. The Florence Griswold Museum still holds those painted panels in place and rotates American Impressionist exhibitions through the adjoining gallery building. Population sits at about 7,500.

The town's eastern edge meets the Connecticut River where it empties into Long Island Sound, and the Roger Tory Peterson Estuary Center (named for the legendary ornithologist and bird-guide author who lived in nearby Old Lyme for decades) leads guided bird walks through the Great Island salt marsh, one of the largest tidal marsh complexes in southern New England. The annual September Swallow Cruise runs at dusk to watch roughly 500,000 tree swallows roost in the marsh reeds.

Old Saybrook

Old Saybrook sits at the mouth of the Connecticut River and includes the Fenwick borough, the seasonal home where Katharine Hepburn spent every summer of her life from age six and where she lived full-time during her last seven years. She died at the rebuilt Fenwick house in 2003 at age 96; she was born in Hartford in 1907, not in Old Saybrook. The Katharine Hepburn Cultural Arts Center, known locally as The Kate, is housed in the 1911 Old Saybrook Town Hall and runs a year-round performing arts schedule alongside a museum of her personal effects, donated by her heirs after her death.

Lynde Point Lighthouse (1838) and the Saybrook Breakwater Lighthouse (1886) both rise from the Connecticut River mouth and feature on the state's "Preserve The Sound" license plate. Harvey's Beach faces Long Island Sound at the south end of town. The town's downtown along Main Street between Old Saybrook Junction and the river runs with independent shops, the seasonal Liv's Oyster Bar, and the long-running Penny Lane Pub, a British-style pub in the 1810 Stevens General Store building.

Westport

Westport runs along the Saugatuck River where it empties into Long Island Sound, about 50 miles by road from Midtown Manhattan and 25 miles east of the Connecticut state line. The town has been a summer escape for New York theater, art, and advertising professionals since the 1930s. The Westport Country Playhouse, opened in 1931 in a converted barn, has staged premieres of work by Arthur Miller, Tennessee Williams, and Wendy Wasserstein; both Joanne Woodward and the late Paul Newman were longtime artistic directors and Westport residents.

The MoCA Westport contemporary art museum opened in 2019 in a renovated industrial space on Newtown Turnpike, with a focus on rotating exhibitions of emerging and established American artists. Sherwood Island State Park, the state's first state park (1914), runs 1.5 miles of beach on Long Island Sound. The Levitt Pavilion next to the Westport Library runs a free summer concert series of about 50 evening shows from late June through August, with everything from acoustic singer-songwriters to jazz quartets.

Bethel

Bethel sits in western Connecticut just south of Danbury and is the birthplace of P.T. Barnum, the showman, who was born on the corner of Greenwood Avenue and Center Street on July 5, 1810. The Bethel Public Library on Greenwood maintains a Barnum collection, and the annual Barnum Festival, headquartered in Bridgeport but with Bethel roots, runs in late June. Greenwood Avenue, the main drag, runs pedestrian-friendly with the kind of indie storefronts that disappeared decades ago in neighboring Fairfield County towns.

The Sycamore Drive-In, opened in 1948 and operating in nearly continuous fashion since, still slings root beer in frosted mugs from a 1950s-style drive-in setup; the Saturday-night Cruise Night between May and September draws hot-rod collectors with a DJ on the lot. Blue Jay Orchards on Plumtrees Road runs 140 acres of pick-your-own apples with 36 varieties; the orchard's apple-cider donuts are widely cited as the best in Connecticut.

Eight Towns On The Sound And The River

The eight Connecticut towns above each set up around one specific geography. Mystic and Madison face Long Island Sound. Essex, Glastonbury, Old Lyme, and Old Saybrook sit along the Connecticut River. Westport faces the Sound from the state's Gold Coast. Bethel runs inland in the western hills. Each one rewards a focused weekend; collectively they cover most of what makes summer in Connecticut work.