Designated one of the best small towns in America, Essex is three distinct villages. Villages are demographic rather than political entities, built around a geographic or economic commonality, said Don Malcarne, a lifelong resident and town historian. While under the same municipal government, Essex, Centerbrook, and Ivoryton each has a post office and ZIP code and a Main Street. Centerbrook drew the earliest settlers, in the late 1600s, when the area was called Potapoug. When the shipbuilding era dawned, the focus shifted to Essex Village, with its easy access to the Connecticut River. The Industrial Revolution and the Victorian era boosted the fortunes of Ivoryton, the home of Comstock, Cheney & Co., one of the country's preeminent manufacturers of ivory piano keys, billiard balls, combs, knitting needles, and toothpicks. Today Centerbrook is the town's commercial center with banks, shops, and light industry. Essex Village draws the most visitors, with its historic houses, shops, and the Connecticut River Museum . Ivoryton boasts summer theater at the Ivoryton Playhouse, formerly a social hall.
DoAn Essex Historical Society (essexhistory.org) brochure maps a self-guided tour along Main Street, describing the historic homes and other buildings. You can download it from the website or pick one up for $1 at the Connecticut River Museum, the Griswold Inn, or the Pratt House Museum.
The Pratt House Museum (19 West Ave., 860-767-0681, essexhistory.org, weekends 1-4 p.m. June through September, free admission) shows how a prominent 18th-century Essex family lived. Seven generations of the Pratt family lived here from 1701 until 1915, and exhibits show how Essex changed from an agrarian society to one in which the building of sailing ships and commerce dominated.
Departing from the steamboat dock at the foot of Main Street, Riverquest (67 Main St., 860-662-0577, ctriverexpeditions.org) offers daytime and sunset cruises, as well as cruises to spot eagles and seals. Daytime trips cruise Essex Harbor and the lower Connecticut River, offering a good view of Gillette Castle. The two-hour sunset cruise is for adults only and participants are welcome to bring a picnic basket and beverages aboard.
RestThe Griswold Inn (36 Main St., 860-767-1776, griswoldinn.com, doubles $100-$370 with continental breakfast), which says it has been in operation since 1776, combines historical charm with modern amenities. The Griswold is also a museum that captures the maritime glory of Essex. The inn is said to have the country's largest private collection of Currier & Ives maritime prints, with their washed-out , dreamlike quality, and Antonio Jacobsen steamship oils, all blue-back ocean and puffy-cloud-filled sky. Guests can choose from a variety of lodgings in five buildings in the heart of Essex Village.
The Copper Beech Inn (46 Main St., Ivoryton, 860-767-0330, 888-809-2056, copperbeechinn.com, doubles $195-$375 including full breakfast) offers luxurious accommodations in a Victorian-era mansion. Formerly the private estate of Archibald Comstock of the S.M. Comstock Co., a leading importer and manufacturer of ivory products, the inn gets its name from a massive copper beech tree on the property.
FuelA favorite of locals is the Black Seal Seafood Grille (15 Main St., 860-767-0233, theblackseal.net, lunch $7-$13, dinner $15-$25). This bar and restaurant has a distinctly maritime feel, with dark wood, exposed beams adorned with oars, and walls decorated with nautical maps and thick coils of rope. There's a good selection of salads and sandwiches at lunch; steak and seafood dominate the dinner menu.
Crow's Nest Gourmet Deli & Bakery in Brewer's Dauntless Shipyard (37 Pratt St., 860-767-3288, breakfast $2-$7, lunch $4-$15) offers soups, salads, sandwiches, and fried seafood in a cozy spot overlooking the marina.
You can pick up breakfast or lunch and take it to the park or the river from the all-takeout Olive Oyl's (77 Main St., 860-767-4909, lunch $5-$8).
The town's top dining rooms are at its signature hotels -- the Griswold and the Copper Beech. The Griswold is famous for its Sunday Hunt Breakfast, a dining convention the inn says was started by the British when they occupied the Griswold Inn during the War of 1812. The Copper Beech features French country cuisine and a wine cellar of more than 5,000 bottles. For a more casual dinner, try the new Brasserie Pip, with French bistro fare and al fresco dining on the porch.
PlayThe Connecticut River Museum (67 Main St., 860-767-8269, ctrivermuseum.org, adults $6, seniors $5, children $3) has lots of child-friendly exhibits designed to show how the Connecticut River shaped the lives of explorers, farmers, shipbuilders, and artisans. Housed in a warehouse on what used to be the steamboat landing, the museum offers ship models, manifests, navigation tools, and a full-scale working reproduction of the "Turtle," the country's first submarine, a clunky, wooden egg-shaped vessel.
For a different perspective on the valley, board the Essex Steam Train (1 Railroad Ave., 860-767-0103, 800-377-3987, essexsteamtrain.com), a coal-fired steam locomotive. An hour-long riverboat cruise is also available May-October. Thomas the Tank Engine visits the first two weekends in November, and there's a seasonal holiday schedule.
PartyThe wine bar at the Griswold Inn offers small plates and flights of wine with fun names such as "Under the Tuscan Sun" and "A Multitude of Zins." There's an intriguing menu of small plates including pumpkin seed-crusted Stonington sea scallops and brie with golden raspberry and Muscat jam and house-made raisins. Behind the bar is a mural of the Connecticut River as it would appear through a porthole.
At the Ivoryton Playhouse (103 Main St., Ivoryton, 860-767-7318, ivorytonplayhouse.org) you can enjoy live theater on a stage that has hosted Katharine Hepburn, Marlon Brando, and Art Carney. This season's schedule includes "Nunsense " through July 1, followed by "Brighton Beach Memoirs ," "Joseph and the Amazing Technicolor Dreamcoat ," the world premiere of "Looped ," and "Tuesdays With Morrie ."
SpendThe French Hen (16 Main St., 860-767-7781) offers French-inspired home decor, including Le Jacquard Français table linens, French lavender, soaps, candles, and bath and beauty products. We particularly liked laser-cut paper lampshades made by Scandinavian artist Tord Boontje .
Its name notwithstanding, Scensibles Unique Boutique (19 Main St., 860-767-7877, scensibles.com) features distinctive jewelry by local artisans, including crystals, sea glass, and freshwater pearls. Lost an earring? The shop will turn your solo earring into a pendant.
The Red Balloon (77 Main St., 860-767-0763) offers high-end children's clothing, including traditional Eton suits, dress coats, and a gorgeous selection of christening dresses.
Wondering what the latest must-have toy is? Your queries will be authoritatively answered by Allen Divoll and Dee Ferris, husband-and-wife owners of Toys Ahoy (43 Main St., 860-767-2067). And it's fun to browse the shelves for LEGO blocks, American Girl, Thomas the Tank Engine, Baby Einstein, Fisher-Price, Webkinz, and other classic and new favorites.