Explore 'the perfect small American town' of Essex, Connecticut

There’s a town in Connecticut where the Fourth of July never truly ends. Walk down Main Street and every storefront is draped in bunting, every porch flies a flag, each one competing to outdo the next in patriotism. The street itself is painted red, white and blue, sloping gently downhill past pristine 18th century homes toward the Connecticut River, where the town dock and a wide green lawn meet the water’s edge. Essex has long been called “the perfect small American town” and standing at that dock looking out over the river, it’s hard to argue otherwise.

In 2026, as America marks its 250th anniversary, it's the perfect place to spend a day or two, as The Griswold Inn, the riverfront town’s historic centerpiece, is celebrating its own 250th anniversary alongside the nation.

Getting there

For Long Islanders, Essex is closer than it feels. The most scenic route is the Cross Sound Ferry out of Orient Point, a 90-minute trip to New London. Standard fare runs $70 for a car and driver, $20 per additional passenger (a floating fuel surcharge applies). From there, it's a 25-minute drive up Route 9 into town.

If you prefer to skip the car, Amtrak runs from Penn Station to Old Saybrook, though you’ll need a 10-minute rideshare to reach Essex. Tickets for the roughly two-hour trip start at $15.

Exploring Main Street

Stroll Essex’s quiet, gaslit streets and you’ll find flower boxes spilling over white picket fences and a mix of Federal, Colonial and Georgian-style homes, each marked with plaques naming the original sea captain and year built. Main Street was laid out in 1748, and the village still follows a compact, walkable cluster of streets anchored by Main, Pratt and Ferry streets, along with West Avenue and nearby side roads.

The Noah Tooker Homestead, built circa 1733, is one of the oldest houses on Main Street. A block away, the Pratt House (19 West Ave.; essexhistory.org), believed to date from between 1701 and 1732, operates as a museum run by the Essex Historical Society (22 Prospect St.; 860-767-0681). Tours are free Saturdays and Sundays through September from 1 to 4 p.m.

There isn’t a box store or national chain in sight: Emmy’s on Main (45 Main St.; 860-767-7877) and The RiverLane (7 Main St.; theriverlane.com; 860-662-4688) offer clothing, artisan jewelry, one-of-a-kind gifts and Essex merchandise; Bluegill Home (45 Main St.; 646-322-5391), Weekend Kitchen (16 Main St.; weekendkitchenct.com; 860-767-1010) and Goods and Curiosities (47 Main St.; store.griswoldinn.com; 860-767-0210) carry curated homewares; JOY Chocolate Co. (5 N Main St.; joychocolateco.com; 860-662-4489) sells handmade chocolates; and Sweet P’s (51 Main St.; sweetpessex.com; 860-767-7805) serves ice cream for the walk back down the hill.

At the foot of Main Street, the Connecticut River Museum (67 Main St.; ctrivermuseum.org; 860-767-8269) sits in a restored 1878 steamboat warehouse, with exhibits on the town’s shipbuilding history and river cruises starting at $35 per person.

The Griswold Inn

The Griswold Inn (36 Main St.; griswoldinn.com; 860-767-1776) is the pulse of Essex and has been since 1776. Known locally as the Gris, it’s like visiting a hotel, restaurant and museum in one; one of the oldest continuously operating inns in the country, it contains the largest private collection of maritime art, displayed throughout its rooms, hallways and dining spaces. 

The inn opened the same year the Oliver Cromwell, the first American Revolutionary War ship built, was constructed just yards away. "All sorts of people came to see this," owner Joan Paul says, "and they needed a place to stay. That's how the Gris came to be."

The inn’s 34 rooms are decorated with fine antiques and start at $265 per night, but the dining is the real centerpiece. The Tap Room, with its domed ceiling of original horsehair-and-clamshell plaster never once altered, predates the inn itself, built in 1738 as Essex's first schoolhouse and rolled down Main Street on logs by oxen. The Covered Bridge dining room was created from a former New Hampshire covered bridge, taken apart piece by piece and rebuilt on-site.

The Gun Room houses firearms dating to the 15th century, including a Revolutionary War musket with a note on display found in the barrel from a father to his son, inscribed the "7th month, 7th day, 1776." The Library dining space surrounds visitors with antique books, a fireplace and steamship oil paintings.

Entrees include chicken madeira ($29), boneless short ribs ($42) and the grilled angus burger ($22) stamped with a "Gris 250" brand. The Revolutionary Ale, brewed exclusively for the inn, is $6, and craft cocktails start at $10. Several nights a week, live sea shanties and piano fill the Tap Room.

The adjacent Wine Bar features an 18-foot "rocking" mural that mimics the roll of a ship at sea and more than 50 wines by the glass. Wine director Nicole Boutilier has designed historic flights for America 250, including the Jeffersonian, a procession of French Burgundy, Rhone whites and Champagne. "These are actually wines that Thomas Jefferson drank," she says. Flights start at $17 and are half price for women on Wednesdays.

Hanging in the Wine Bar is a pencil sketch by Norman Rockwell titled "Steamboat Race on the Connecticut," painted around 1940 and considered his only purely nautical work.

Essex Steam Train and Riverboat

Head to the Essex Steam Train (1 Railroad Ave.; essexsteamtrain.com; 860-767-0103) for a ride that blends history with scenery. One of the few fully operable steam railroads in the country, it carries passengers in restored 1920s-era cars, including a 1930 Pullman once used on the Yankee Clipper between Boston and Grand Central. The 1.5-hour trip travels through the Connecticut River Valley to Chester and back.

An optional connection in Deep River adds a riverboat cruise, offering a water-level view of the valley and sights like Gillette Castle, the medieval-style home built by actor William Gillette in 1914. Wildlife sightings can include bald eagles and herons. Train tickets start at $30; the combined train-and-boat excursion costs $65.

On select weekends, brunch and dinner trains feature three- or four-course meals served during a 2.5-hour ride in a Pullman car, starting at $109 per person. The popular North Pole Express runs from mid-November through Christmas and typically sells out; tickets go on sale Aug. 3 and start at $60.

Where to eat

For breakfast, stop by Essex Coffee and Tea Co. (51 Main St.; essexcoffee.com; 860-767-7804) for coffee, tea and baked goods, or head to Olive Oyl’s (6 Main St.; oliveoylscarryout.com; 860-767-4909), a local institution since 1991 housed in a former gas station, where vintage Mobil Pegasus signage still lines the walls. A standout is the smoky, spicy linguica egg-and-cheese with Portuguese sausage on a Portuguese English muffin ($10).

For lunch or dinner, Drift (37 Pratt St.; eatdrinkdrift.com; 860-662-4275), the newest addition, sits at Safe Harbor Dauntless Shipyard with water views and a menu of elevated coastal fare. The ahi tuna nachos ($23) make a strong start, but the lobster dishes are the draw: the Mardi Claw roll ($44) features Cajun butter-poached lobster with crispy andouille crumble and remoulade, and the lobster “rangoonz” ($20) are also worth ordering.

Outdoor activities nearby

Kayak and paddleboard rentals are available through Black Hall Outfitters (132 Shore Rd.; blackhallmarina.com; 860-785-9520) in nearby Old Lyme, offering an easy way to explore the Connecticut River and nearby coves.

Golfers can choose between Fenwick Golf Course (580 Maple Ave.; fenwickgolfcourse.com; 860-388-2516) in Old Saybrook and Fox Hopyard Golf Club (1 Hopyard Rd.; foxhopyard.com; 860-434-6644) in East Haddam, with Essex Indoor Golf Center (23 Saybrook Rd.; essexindoorgolf.com; 959-265-8979) as a backup on rainy days. Tennis courts and a playground sit just behind Town Hall in Essex on West Avenue.