Written by Caryn Davis
July 2018

ESSEX CONNECTICUT, is a quintessential New England village located on three bodies of water — the Connecticut River, Middle Cove and North Cove, making it ideal for cruising. Tree-lined Main Street features immaculately restored Colonial- and Federal-era homes that house residents, restaurants and shops. Some of these beautiful structures bear the names of sea captains who once occupied them. It’s unmistakably peaceful and picturesque, yet upbeat and lively with plenty to see and do.

Essex Connecticut is home to three marinas with transient slips and moorings: Brewer Dauntless Shipyard & Marina, Brewer Essex Island Marina and Middle Cove Marina, all within a two-minute walk to buzzing Main Street. Brewer Essex Island Marina also boasts Marley’s Café, known for its delicious jerk chicken and live reggae music.

Overlooking Essex Harbor at the foot of Main Street lies the Connecticut River Museum. In the 18th- and 19th-centuries, coastal schooners and later steamships docked here to unload their cargo and pick up passengers. It’s the only museum on the entire 400-mile river dedicated to preserving the story of the river and its people. The museum also houses a town dock that is ideal for casting a line to fish. Directly across from the museum sits Nott Island Wildlife Preserve, offering beach access on the northwest side that is suitable for swimming. You can explore the island’s scenic 82 acres on foot or by kayak.

A few steps from the museum, visitors find the Griswold Inn, which predates the Revolutionary War. The inn’s Tap Room has a barrel- vaulted ceiling, delectable food, grog and entertainment. Adorning the walls is a collection of steamboat art, ephemera and antique guns. Around the corner from “The Gris” is Boatique USA. This nautical shop offers everything you need to outfit your boat’s interior, including custom-made, waterproof bedding.

DAY ONE

MYSTIC 25.5 NM

After breakfast at the Crow’s Nest in Brewer Dauntless Shipyard & Marina in Essex Connecticut, head south for Long Island Sound on the mouth of the river in Old Saybrook, less than four nautical miles away. Be sure to stay in the channel, as it is easy to run aground due to eternally shifting sandbars that saved the river from development.

Heading east, you will pass bucolic Old Lyme, Black Point and Niantic Bay, emptying you into the Niantic River. Long Island Sound becomes Fishers Island Sound near the tiny fishing village of Noank, which is also where the Mystic River begins. Enjoy the view as the river narrows and meanders past marshes, pristine homes and the exclusive Mason’s Island.

Brewer Yacht Yard at Mystic is on the river, 15 minutes from the Sound and just south of the Mystic River Railroad Bridge. If you are going on to Mystic Seaport, pay heed that both this and the Mystic River Bascule Bridge have scheduled openings. Mystic Seaport is a living museum housed in an authentic 19th-century New England coastal village and also offers visitors hands-on boat building workshops and other maritime courses.

Mystic Seaport is within a quick jaunt to town when following the river. With its Victorian streetscape, it’s easy to imagine how Mystic must have looked when it was established as a shipbuilding community more than 200 years ago. The boutiques, bars and restaurants are plentiful. Next to the drawbridge, the S&P Oyster Company offers great views while dining al fresco on seafood. Be sure to check out Captain Daniel Packer Inne — once used as a stopover for fatigued sailors traveling between Boston and New York. Many mariners still congregate at the Inne to eat, drink and listen to music.

DAY TWO

WATCH HILL 9 NM

Follow Fishers Island Sound east along the coast past Stonington to Watch Hill, R.I. Along the way, enjoy a stop and swim at Sandy Point Island, a 35-acre island in Little Narragansett Bay. Watch Hill Harbor is situated on Watch Hill Cove. While there is no marina, Watch Hill Docks is nestled in the heart of the village and offers fantastic amenities. You can swim in the calm, clear waters of the cove or cross over the dunes to Napatree Point Beach, a beautiful wildlife preserve that’s great for sunbathing, swimming, walking and bird watching.

Watch Hill has changed very little from its Victorian origins as a summer resort town for affluent families and is still home to the wealthy, including pop sensation Taylor Swift, whose $17 million house sits on top of the bluff the town is named after. There are a few shops and eateries along Bay Street, including the 102-year old Olympia Tea Room for elegant bistro-style cuisine. Across from the eatery is the hand-carved Flying Horse Carousel, circa 1876. It is believed to be the oldest carousel in the country and was part of a traveling carnival.

Travel just past the carousel to a peninsula that leads to Watch Hill Lighthouse, and then continue to Bluff Avenue to the more crowded East Beach on the Atlantic side to catch the waves. It’s hard to miss the large and  opulent Ocean House — built in 2004 after the original 135-year old hotel was unfortu-nately demolished due to neglect. While overnight guests have access to a private stretch of East Beach, you can still eat and drink on their wrap-around veranda or in the restaurant.

DAY THREE

WICKFORD 39.1 NM

Follow the coast north to historic Wickford, located on the west side of Narragansett Bay inside the scenic Wickford Harbor and surrounded by four coves. Wickford was founded in 1663 and boasts the largest collection of colonial houses in the Northeast with 95% of the original village still in tact. Author John Updike, who penned “The Witches of Eastwick,” is a direct descendent of Wickford’s founding fathers, and many consider his famous novel to have been set in this town. Once detached from the mainland, Wickford still retains a relaxed island vibe.

Boaters can overnight at Brewer’s Wickford Cove Marina or at Wickford Marina on Mill Cove, a 40-acre wildlife preserve that encompasses Rabbit Island and Conanicus Island, named after a Narragansett chief. The town has five transient moorings in the outer harbor that are free of charge and are occupied on a first-come, first-serve basis. The town also maintains 160 feet of transient docks overlooking the harbor with a two-hour limit.

The John H. Chafee Nature Preserve is another area to discover by foot or kayak. It has 230 acres with trails leading to Narragansett Bay. Near Wickford Cove at the end of Beach Street is the North Kingstown Town Beach, sometimes referred to as Cold Spring Beach. It offers a roped-off area for swimming, a grassy area with tables and grills for picnicking and a playground. If you prefer to wander by bike and brought your fold-up bike onboard, head to Wilson Park Bikeway — a 1.5-mile loop through the 75-acre Wilson Park. Along the path, you will discover great places to picnic or explore hidden coves.

Wickford offers loads of gift shops, seafood markets and restaurants with waterfront dining, and practical stores for provisions. The town also hosts a bevy of regattas, festivals, fairs, parades and even an air show. But with all this activity, do not underestimate the simple pleasure of taking a walking tour around the village to see 20 key historical houses and buildings or visiting the Quonset Air Museum, Smith’s Castle, Seabee Museum or the Gilbert Stuart Birthplace & Museum.