Top 15 Activities to Experience in Old Saybrook, CT

With a history that can be traced back to a colony in 1635, Old Saybrook is a serene coastal town located at the mouth of the Connecticut River.

Actress Katharine Hepburn (1907-2003) relocated to Old Saybrook’s affluent borough of Fenwick in 1912 and frequently returned to her family residence throughout her life, ultimately retiring here in 1997. In 2009, a dedicated museum and theatre opened on Main Street in her honor.

Like many premier towns along the Connecticut shoreline, Old Saybrook offers sandy beaches, antique shopping, historic house museums, exquisite dining options, and fishing charters.

The concluding segments of the Connecticut River present breathtaking scenery, which can be appreciated at waterfront parks or on an combined steam train and riverboat excursion departing from nearby Essex.

Let’s delve into the finest activities available in and around Old Saybrook, Connecticut:

1. The Katharine Hepburn Cultural Arts Center

A proper tribute to the legendary actress and Old Saybrook native, this theater and museum was established in Old Saybrook’s former town hall in 2009. The Colonial Revival structure, featuring a prominent Doric portico, dates back to 1911 and is listed on the National Register of Historic Places.

The initiative was completed with the full endorsement of the Hepburn estate, and the museum was curated with contributions from Katharine’s brother-in-law.

Visitors can view rare photographs from her life and career, along with historical movie posters, a self-portrait painted by her, and an Emmy award she received.

Regarding performances, the program offers a diverse selection of plays, various styles of live music, contemporary and classical dance, evenings with prominent personalities, and broadcasts from cultural institutions like London’s National Theatre.

2. Harvey’s Beach

Frequently recognized as one of the finest municipal beaches on the Connecticut shoreline, Harvey’s Beach spans 100 meters of pristine white sand.

The difference in beach size between high and low tide is considerable, allowing visitors to walk far out when the tide is low, remaining in shallow water due to the offshore sandbars.

This characteristic makes Harvey’s Beach an ideal location for children to wade and play in Long Island Sound.

Many individuals take their chairs out to the dry sandbars during low tide; however, one must be prepared to relocate as the tide returns.

Lifeguards are present from Memorial Day Weekend to Labor Day, and a concession stand and restroom facilities are available throughout this period.

Weather permitting, outdoor concerts can also be enjoyed on Friday evenings.

Dogs are permitted from October to May.

3. Fort Saybrook Monument Park

This park, located at Saybrook Point at the mouth of the Connecticut River, is historically significant as the site of the Saybrook Colony.

The colony was established in 1635 by John Winthrop the Younger (1606-1676), who played a crucial role in merging several separate settlements and later became Governor of the Connecticut Colony during 1657-58. The fort built at this location in 1635 was named in honor of Lord Say and Sele and Lord Brooke, to whom these lands had been granted.

A boardwalk traverses the riverside marsh, with informational plaques detailing the historical significance of this location.

In the 19th century, this area served as the terminus for the Connecticut Valley Railroad, with remnants of the roundhouse and turntable still visible.

Nearby, you will find the Mini-Golf at Saybrook Point, operational from Memorial Day weekend through Columbus Day weekend, complete with a concession stand.

4. General William Hart House

To gain insights into Old Saybrook’s heritage as a port and shipbuilding hub, visit the Old Saybrook South Green historic district, where the structures date from the 1760s to the 1900s.

A notable site is the Colonial-style General William Hart House, constructed around 1767 by a merchant who would later serve in the Revolutionary War and become a candidate for Governor of Connecticut.

Intriguingly, the building features details more commonly associated with homes in Williamsburg, Virginia, and Dutch Pennsylvania.

Currently operated by the Old Saybrook Historical Society, guided tours provide fascinating information about the decor, artifacts, and the history of the Hart family.

After acquiring the house in 1974, the society landscaped the previously overgrown yard into a Colonial-style formal garden featuring shrubs, perennials, roses, and an espalier pear tree against the south wall of the house.

5. Essex Steam Train and RiverBoat

At the historic Essex Station (1892), embark on a 2.5-hour journey through the Connecticut River Valley and along the river itself.

The Train & Boat excursion begins with a ride in vintage coaches pulled by a steam locomotive, passing through picturesque towns such as Deep River and Chester, complemented by views of pristine nature at Selden Neck State Park and the tidal wetlands of Pratt Cove and Chester Creek.

Be on the lookout for wading birds and waterfowl such as egrets, herons, ducks, and cormorants, while bald eagles migrate to this region during February and March.

Upon arriving at Deep River Landing, guests board the multi-decked Becky Thatcher riverboat to appreciate the natural beauty of the valley, alongside impressive landmarks including Goodspeed Opera House (1876-77) and Gillette Castle (1914), before returning to Deep River Landing for the return train trip to Essex.

6. Connecticut River Museum

You could not select a more suitable location for this museum than the majestic final stretch of the Connecticut River before it flows into Long Island Sound.

The Connecticut River Museum is housed in a former steamboat warehouse from 1878, located on Steamboat Dock in the charming Essex Village.

Three permanent exhibits are available for exploration, showcasing the human history of the Connecticut River up to the 19th century, the river’s captivating natural history, and a “Vertical Mural” illustrating all 410 miles of the watercourse.

In 2019, an exhibition focused on eagles in the Connecticut Valley complemented the annual model railroad display by local enthusiast Steve Cryan, featuring new themes each year.

The museum also serves as the docking point for the Onrust (Dutch for Restless), a faithful replica of the ship sailed by the Dutch fur trader Adriaen Block (1567-1627). Onrust departs for cruises Thursdays through Mondays and is open for tours when docked.

7. Essex Village

Seize the opportunity to stroll along Main Street in the charming Essex Village, situated on a narrow tract of land jutting into the Connecticut River estuary.

Main Street and the adjoining roads feature Georgian and Federal-style homes adorned with painted shutters and quaint gardens behind picket fences.

At No. 36, you will find the Griswold Inn, a historic establishment that has been operational since 1776. With water on three sides, Essex Village invites exploration of galleries, studios, unique boutiques, taverns, and tea shops, leading you toward the Essex Town Dock by the River Museum at the eastern tip.

Here, one can relax on the boardwalk, taking in the expansive view of the CT River and observing the maritime activity heading into and out of Long Island Sound.

8. The Preserve

Until 2015, this unspoiled area in Old Saybrook was the largest expanse of unprotected coastal forest between New York and Boston.

The Preserve, safeguarded by the Trust for Public Land, is partially owned by the town, the Essex Land Trust, and the State of Connecticut.

This 963-acre area boasts diverse ecosystems, including mature coastal forests, vernal pools, rare swamp habitats, and the headwaters or tributaries of the Oyster River, Mud River, and Trout Brook.

Visitors can hike in the central and northern sections of The Preserve, utilizing 10 miles of trails that navigate through a wildlife-rich environment.

A total of 57 bird species and 30 mammal species have been recorded here, along with amphibians and reptiles such as box turtles, spotted turtles, and northern dusky salamanders.

9. Florence Griswold Museum

Essential for any enthusiast of American art, this late-Georgian house located nearby in Old Lyme was the nexus for American Impressionism.

The Old Lyme Art Colony originated at a boarding house managed by Florence Griswold (1850-1937), where prominent Impressionists such as Henry Ward Ranger, Childe Hassam, Edward Charles Volkert, and Willard Metcalf were regular visitors.

In a tradition resembling French art colonies, the artists contributed paintings during their stays, and a total of 41 painted panels can be found in the ground-floor rooms.

The museum has an impressive art collection, featuring works by Milton Avery, Hassam, Matilda Browne, Bessie Potter Vonnoh, Frederic Church, and others.

The museum consists of the historic house and the bright and airy Krieble Gallery, which opened in 2002. A brief, engaging film shares the story of the colony, and visitors can learn delightful anecdotes about the artists’ experiences during their stays in the house.

10. Rocky Neck State Park

If you’re seeking another location to relax along Long Island Sound, Rocky Neck State Park is a mere ten minutes from I-95 and ranks among the most frequented state parks in Connecticut.

The park’s allure lies not only in its white sandy beaches but also in the significant natural habitats of salt marsh, rocky shoreline, and a tidal river.

A noteworthy man-made feature is the Rustic-style pavilion, constructed during the Great Depression of the 1930s as part of a Works Progress Administration project.

At over 110 meters in length, this is the largest Depression-era structure in Connecticut.

Hiking trails lead you through the salt marsh, past the shipyard, and to a cave, and there is a campground with 160 sites available.

11. Ferry Landing State Park

Even closer, Ferry Landing State Park is situated right at the mouth of the Connecticut River, on the Old Lyme side.

This stunning location provides numerous reasons to visit, whether to observe boats gliding by from the boardwalk or to enjoy the scenic view across to Old Saybrook, including the steel railroad bridge that opens for large vessels.

This area also serves as a prime spot for fishing and crabbing (blue crabs are prevalent), as well as for wildlife observation.

Seals can be spotted in the water, and sightings of ospreys or shorebirds in the neighboring saltmarsh are not uncommon.

Additionally, this park is the DEEP Marine headquarters, where informative resources about local ecology and other state parks are available during business hours.

12. Essex Saybrook Antiques Village

This antiques center on the Middlesex Turnpike epitomizes the types of businesses one hopes to discover along the New England shoreline, featuring over 50 different dealers.

Time spent here can easily fly by as you navigate through furniture, vintage signs, collectibles, jewelry, antique sports memorabilia, old home appliances, lighting, ceramics, art, textiles, children’s toys, military artifacts, and model boats.

Essex Saybrook Antiques Village is situated within a charming complex of one-story clapboard buildings and is open seven days a week from April through December.

13. Lynde Point Light

Although this lighthouse, in its current form since 1839, is situated on private property, it remains a worthwhile destination as it commands a view at the tip of a peninsula overlooking the mouth of the Connecticut River.

You can reach it via Sequassen Avenue, park to admire the view, and then continue on your way.

On a granite pier, the 20-meter lighthouse is celebrated for its highly crafted tapering brownstone walls.

The beacon was originally lit with whale oil until 1879, transitioned to kerosene, and underwent electrification in 1955. Lynde Point Light is currently operational, having been automated by the United States Coast Guard in 1978.

14. Westbrook Outlets

There are substantial discounts on premier brands available at this quaint outlet mall located five minutes west in Westbrook.

The mall is conveniently situated just half a mile from the shoreline, featuring over 50 brand name outlet stores including Old Navy Outlet, J. Crew Factory, H&M, Eddie Bauer Outlet, Carter’s, Williams Sonoma Outlet, and Sunglass Hut.

If visiting on a rainy day, a 12-screen multiplex theater at Marquee Cinemas is located adjacent to the mall.

A more conventional mall, which is not as much of a shopping attraction but more of a place to acquire necessities, can be found closer to home at the Old Saybrook Shopping Center, easily visible from the Boston Post Road. It includes retailers such as Walmart, Gamestop, HomeGoods, Stop & Shop, and Marshalls.