With a history that can be traced back to a colony in 1635, Old Saybrook is a placid coastal town at the mouth of the Connecticut River.
Actress Katharine Hepburn (1907-2003) moved to Old Saybrook’s posh borough of Fenwick in 1912 and would return to her family home throughout her life, retiring here in 1997. In 2009 a museum and theatre opened on Main Street in her honor.
Like all the best towns on the Connecticut shoreline, Old Saybrook promises sandy beaches, antiques shopping, historic house museums, great food and fishing charters.
The final reaches of the Connecticut River are wonderfully scenic, and you can take in this natural beauty at waterfront parks or on a combined steam train and riverboat journey from nearby Essex.
Let’s explore the best things to do in and around Old Saybrook, Connecticut:
1. The Katharine Hepburn Cultural Arts Center
A fitting tribute to the iconic actress and Old Saybrook native, this theater and museum was set up in Old Saybrook’s former town hall in 2009. The Colonial Revival building, with a striking Doric portico, dates back to 1911 and is on the National Register of Historic Places.
The project was completed with the full support of the Hepburn estate, and the museum inside was even curated with the help of Katharine’s brother-in-law.
You can peruse seldom-seen photographs from her life and career, together with contemporaneous movie posters, a self-portrait that she painted and an Emmy award she won.
As for performances, there’s a big mix of plays, live music of all kinds, contemporary and classical dance, evenings with important personalities and broadcasts from cultural institutions like London’s National Theatre.
2. Harvey’s Beach
Often hailed as one of the best town beaches on the Connecticut shoreline, Harvey’s Beach is 100 meters of white sand.
The difference between the size of beach at high and low tide is dramatic, and when the water is out you can walk a long way out before the water gets above waist height thanks to the offshore sandbars.
This obviously makes Harvey’s Beach a safe place for children to wade and play in Long Island Sound.
Many people even take their chairs out to the dry sand bars at low tide, but you’ll need to be ready to move when it comes back in.
There are lifeguards here from Memorial Day Weekend to Labor Day, while a concession stand and restrooms are open throughout this time.
Depending on the weather you can also catch an outdoor concert on Friday nights.
Dogs are welcome from October to May.
3. Fort Saybrook Monument Park
No ordinary park, this spot at the end of Saybrook Point at the mouth of the Connecticut River is the site of the Saybrook Colony.
This was established in 1635 by John Winthrop the Younger (1606-1676), who played a vital role in merging several separate settlements and would later become Governor of the Connecticut Colony in 1657-58. The fort that he 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.
There’s a boardwalk through riverside marsh, and information plaques make clear the importance of this site.
In the 19th century this would be the end of the line for the Connecticut Valley Railroad’s, and the vestiges of the roundhouse and turntable are still visible on the ground.
A moment away on foot is the sweet Mini-Golf at Saybrook Point, open Memorial Day weekend through Columbus Day weekend, and including a concession stand.
4. General William Hart House
You can get a handle on Old Saybrook’s heritage as a port and shipbuilding center at the Old Saybrook South Green historic district, where the contributing buildings date from the 1760s to the 1900s.
A standout is also one of the oldest and can be visited between mid-June and Labor Day.
The Colonial-style General William Hart House was built around 1767 by a merchant who would later serve in the Revolutionary War and become a candidate for Governor of Connecticut.
A curious thing about the building is the amount of detail that is more commonly found in houses in Williamsburg, Virginia and Dutch Pennsylvania.
Now the house is the home of the Old Saybrook Historical Society, and on a tour you’ll be given lots of interesting info on the decor, artifacts and the history of the Hart family.
After acquiring the house in 1974, the society set about turning the overgrown yard into a Colonial-style formal garden with shrub, perennials, roses and an espalier pear tree on the house’s south wall.
5. Essex Steam Train and RiverBoat
At the historic Essex Station (1892) you can set off on an 2.5-hour odyssey into the Connecticut River Valley and on the river itself.
A Train & Boat trip begins with a ride in vintage coaches pulled by a steam locomotive through the picture perfect towns of Deep River and Chester, with panoramas of unblemished nature at Selden Neck State Park and the tidal wetlands of Pratt Cove and Chester Creek.
Keep a lookout for waders and waterfowl like egrets, herons, ducks and cormorants, while bald eagles migrate to this area in February and March.
At Deep River Landing you’ll step aboard the multi-decked Becky Thatcher riverboat to soak up the natural beauty of the valley, and impressive landmarks like Goodspeed Opera House (1876-77)and Gillette Castle (1914), before returning to Deep River Landing for the return train to Essex.
6. Connecticut River Museum
You couldn’t pick a more appropriate place for this museum than the epic final reach of the Connecticut River before it empties into Long Island Sound.
The Connecticut River Museum is in a former steamboat warehouse dating from 1878, on Steamboat Dock at picturesque Essex Village.
There are three permanent exhibits to peruse, charting the human history of the Connecticut River up to the 19th century, the river’s absorbing natural history and a “Vertical Mural” depicting all 410 miles of the watercourse.
In 2019 there was a display about eagles in the Connecticut Valley and the annual model railroad by local enthusiast Steve Cryan, presenting a new theme every year.
The museum is also 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, but is also open for tours when in dock.
7. Essex Village
Take the chance to wander along the Main Street in the adorable Essex Village, on a little thumb of land poking into the Connecticut River estuary.
Main Street and the streets leading off it are all Georgian and Federal houses with painted shutters and dainty gardens behind picket fences.
At No. 36 stands the Griswold Inn, which has been in business since 1776. There’s water on three sides in Essex Village, and as you investigate galleries, studios, one-off boutiques, taverns and tea shops you’ll be drawn to the Essex Town Dock by the River Museum at the eastern point.
There you can sit on the boardwalk to survey the enormous breadth of the CT River and watch the water traffic heading in and out of Long Island Sound.
8. The Preserve
Until 2015 this untouched space in Old Saybrook was the largest swathe of unprotected coastal forest between New York and Boston.
The Preserve was protected by the Trust for Public Land and pieces are owned by the town, the Essex Land Trust and the State of Connecticut.
In these 963 acres are a diversity of ecosystems, including mature coastal forest, vernal pools, rare swamp habitats and headwaters or tributaries of the Oyster River, Mud River and Trout Brook.
You can hike in the middle and northern parts of The Preserve, on 10 miles of trails in an environment bursting with wildlife.
Some 57 bird species and 30 types of mammal have been sighted here, as well as amphibians and reptiles like box turtles, spotted turtles and northern dusky salamanders.
9. Florence Griswold Museum
Unmissable for any fan of American art, this late-Georgian house moments away in Old Lyme was the epicenter for American Impressionism.
The Old Lyme Art Colony was born at a boarding house run by Florence Griswold (1850-1937) where leading Impressionists like Henry Ward Ranger, Childe Hassam, Edward Charles Volkert and Willard Metcalf all stayed.
In the tradition of French art colonies, the artists contributed paintings for the house during their stay, and there are 41 painted panels to be found in the downstairs rooms.
The museum has a formidable art collection of its own, with pieces by Milton Avery, Hassam, Matilda Browne, Bessie Potter Vonnoh, Frederic Church and more.
The museum is made up of the historic house and the bright and airy Krieble Gallery, opened in 2002. There’s a short, entertaining movie telling the story of the colony, and at the house you’ll pick up lots of fun anecdotes about what the artists got up to during their stays.
10. Rocky Neck State Park
If you’re searching for another place to lie back on Long Island Sound, Rocky Neck State Park is ten minutes on the I-95 and one of the most visited state parks in Connecticut.
The park’s appeal is undeniable for its white sandy beaches, but there are also important natural habitats of salt marsh, rocky shoreline and a tidal river.
One manmade feature worth of mention is the Rustic-style pavilion, built during the Great Depression in the 1930s as Works Progress Administration project.
At more than 110 meters long this is the largest Depression-era structure in Connecticut.
Hiking trails take you to the salt marsh, shipyard and a cave, and there’s a campground with 160 sites.
11. Ferry Landing State Park
Even closer, Ferry Landing State Park is right at the mouth of the Connecticut River on the Old Lyme side.
There are plenty of reasons to head to this beautiful spot, to watch the boats gliding by from the boardwalk or to admire the view over to Old Saybrook and down to the steel railroad bridge, which opens to let large boats through.
This is also a prime location for fishing and crabbing (blue crabs are common), but also observing wildlife.
There are seals in the water, and it’s not unusual to see ospreys or shorebirds in the neighboring saltmarsh.
This park is the DEEP Marine headquarters, where you can get hold of information on the local ecology and other state parks during business hours.
12. Essex Saybrook Antiques Village
Exactly the sort of business you’d hope to come across on the New England shoreline, this antiques center on the Middlesex Turnpike boasts more than 50 different dealers.
An hour or two will fly by here, as you pick your way through furniture, vintage signs, collectibles, jewelry, antique sports equipment, old home appliances, lighting, ceramics, art, textiles, children’s toys, militaria and model boats.
The Essex Saybrook Antiques Village is in a pretty complex of one-story clapboard buildings and is open seven days a week, April through December.
13. Lynde Point Light
Even though this lighthouse, dating in its current form to 1839, is on private property, it’s worth making the trip as it sits at the very end of a finger of land looking back at the mouth of the Connecticut River.
You can get there on Sequassen Avenue, park up to appreciate the view and then carry on your way.
On a granite pier, the 20-meter lighthouse is noted for the high workmanship of its tapering brownstone walls.
The beacon was lit with whale oil up to 1879 when it switched to kerosene, before being electrified in 1955. Lynde Point Light is still in service, having been automated by the United States Coast Guard in 1978.
14. Westbrook Outlets
There are big discounts on top brands at this village-like outlet mall five minutes west in Westbrook.
The mall is just half a mile from the shoreline, and among more than 50 brand name outlet stores are Old Navy Outlet, J. Crew Factory, H&M, Eddie Bauer Outlet, Carter’s, Williams Sonoma Outlet and Sunglass Hut.
If you come on a rainy day there’s a 12-screen multiplex at Marquee Cinemas right next door to the mall.
There’s a more conventional mall closer to home at the Old Saybrook Shopping Center, which is hard to miss from the Boston Post Road.
Less a shopping destination and more a place to grab essentials, the mall has a Walmart, Gamestop, HomeGoods, Stop & Shop and Marshalls.