Old Saybrook and Essex: Boating the Lower Connecticut River

The lower Connecticut River is widely regarded as one of the region’s last great natural estuaries, and for boaters it offers a rich combination of scenic cruising, historic towns and well-equipped marinas. At the river’s mouth sits Old Saybrook, and roughly six miles upstream lies Essex — two convenient bases for exploring this beautiful stretch of the Connecticut River and Long Island Sound.

Old Saybrook: Historic Harbor with Modern Amenities

Settled in 1635, Old Saybrook is a lively town of about 10,000 residents that blends New England history with contemporary comforts. The waterfront welcomes visiting boaters with a number of marinas, from the upscale Harbor One and Saybrook Point facilities to transient dockage options at Old Lyme Dock Co. Saybrook Point, marked by the Saybrook Breakwater Light, is the primary river entrance; note that tidal currents can be strong, especially on an ebb tide, so approach with caution and follow channel markers closely.

On the east side of the lower river, shoals and old stone shad piers sit just below the surface, making accurate navigation essential. Channels are well-marked, and several marinas — including Between the Bridges, S&S Marine, Ferry Point, Brewer Ferry Point and Island Cove — provide fuel and basic services. Larger yachts can find care at facilities that service vessels up to and beyond 100 feet, and a West Marine store is located a few miles inland in town for parts and gear.

Things to Do in Old Saybrook

Old Saybrook is ideal for a mix of on-water and onshore activities. The Katharine Hepburn Cultural Arts Center stages concerts, theater and classic film screenings, honoring the town’s famed resident. For relaxation, Saybrook Point Inn & Spa offers spa treatments and waterfront views. Outdoor options include a stroll through the 17-acre Fort Saybrook Monument Park or kayaking the coastal estuaries and backwater streams to experience wildlife and tidal scenery up close.

Dining in Old Saybrook ranges from high-end seafood at Fresh Salt to casual lobster rolls and shellfish at Liv’s Shack and Liv’s Oyster Bar. Johnny Ad’s has served fried seafood, burgers and hot dogs since 1957 and remains a local favorite. Main Street offers breakfast at Paperback Café, pub-style meals at Penny Lane Pub, and family-friendly pizza with a unique model-train feature at Pizza Works. For supplies, there’s a Stop & Shop and a Walmart in town, plus specialty shops and the long-standing Ted’s Bait & Tackle and Rivers End Tackle for anglers seeking local knowledge and tackle.

Essex: Quiet Charm and Riverfront Culture

Just upriver, Essex preserves classic New England character and a quieter pace that many boaters find appealing. The town’s tree-lined streets and historic homes make it an excellent place to stroll and explore. Essex Harbor is among the most picturesque on the Connecticut River, with three marinas offering a range of services.

The Connecticut River Museum, housed in a 19th-century riverside warehouse, highlights the river’s maritime history and hosts seasonal concerts and sunset sails aboard vintage vessels. The museum’s annual Mahogany Memories boat show draws fine examples of classic wooden boats and is a highlight for enthusiasts.

Marinas, Services and Dining in Essex

Essex Boat Works and Brewer Dauntless Shipyard & Marina are full-service facilities with Travelifts and transient berthing for visiting boats. Brewer Essex Island Marina also welcomes transient visitors and has its own café amenities. Boaters looking for grab-and-go provisions will find Olive Oyl’s on Main Street, while the Black Seal pub provides a lively local atmosphere and a menu of pub favorites.

No visit to Essex is complete without stopping at the Griswold Inn, a storied establishment that dates back centuries and offers both classic dining and a notable collection of marine art; it’s also known for its Sea Chanty Night entertainment. For unique land-based outings, the Essex Steam Train & Riverboat offers scenic and dinner-train excursions up the river. Nearby, the Ivoryton Playhouse presents live theater, and the Copper Beech Inn provides upscale lodging and gourmet dining for those seeking comfort ashore.

Practical Tips for Boaters

When cruising the lower Connecticut River, pay careful attention to currents and channel markers, especially near the Saybrook breakwaters and the shallow eastern reaches. Plan fuel and provisioning stops in advance, and use the range of marinas that cater to both transient visitors and larger yachts. Take advantage of local knowledge at tackle shops and marina offices to learn about seasonal conditions and recommended anchorages or moorings.

Both Old Saybrook and Essex welcome visiting boaters with services, dining and cultural attractions, making this stretch of the river an inviting destination for day trips or extended stays. Whether you are seeking lively waterfront dining and entertainment or a peaceful riverside escape, the lower Connecticut River offers a memorable boating experience.

This article originally appeared in the November 2017 issue.