Old Saybrook is one of Connecticut’s oldest towns, settled in 1635 and nestled snugly between Boston and New York, where the Connecticut River laps against Long Island Sound.
It is located in Middlesex County and includes the incorporated borough of Fenwick and the census-designated spots, Old Saybrook Center and Saybrook Manor.
A pretty town brimming with colonial history, Old Saybrook flows with the quintessential charm of New England.
Here anyone can stroll along the stunning shorelines, lounge on sandy strands, dine on patios overlooking the Sound, and absorb history in old mansions.
Its Main Street is lined with a vibrant collection of restaurants and shops, and its community revels in arts and crafts showings, boat shows, sidewalk sales, fireworks displays, outdoor concerts, carol singing, and theatrical works all year.
At Old Saybrook, indulge in recreations, shows and spectacles, shopping sprees, dining opportunities, celebrations, and a trove of culture and history.
There is something in Old Saybrook to please, entertain, and energize those who embark on its shores.
If you don’t know where to start, here is a list of some of the best things you can do while in Old Saybrook:
See the Beauty of Lynde Point Lighthouse
People know New England for its amazing lighthouses, one of which can be found right in Old Saybrook.
Built in 1803, this lighthouse has stewarded ships into Long Island Sound from the mouth of the Connecticut River for centuries.
The original building rose 35 feet above the harbor entrance but was replaced in 1838 by the octagonal brownstone tower seen today, rising at 65 feet and noted for its high workmanship.
It was lit with whale oil until it switched to kerosene in 1879 and then became electrified in 1955.
In 1852, the original lamps were replaced with a 4th order Fresnel lens and then with a 5th order Fresnel lens in 1890.
The lighthouse became fully automated in 1978.
The best place to spot it is by boat, and you can even catch the sunset on the lighthouse as it stands over the water.
Walk Down Main Street
Main Street on Old Saybrook will take you back in time with its Americana-soaked shops, restaurants, and establishments that have inspired countless Hollywood movies.
It is wide and easily walkable and serves as the town’s main retail hub, the most popular spot where one can cruise, shop, grab a bite to eat or drink a cup of coffee.
The street is home to Maximus Antiques, where you can find a showroom bursting with quaint finds: jewelry, dishes, old chairs, and more.
Chase the shabby chic aesthetic at Cottage Flair with its rustic décor, or browse artisan vintage works at Pieces Home Décor.
Shop for the perfect vacation outfit at Pearls and Plaid, or look up the latest styles, designs, and accessories at Saybrook Home.
And when you crave delicious fare and a sweet glass of wine, duck into Penny Lane Pub or Sip Wine Bar.
Taste Seafood at Liv’s Oyster Bar and Restaurant
Liv’s Oyster Bar and Restaurant opened in 2006, and fast became a prime dining destination in Old Saybrook.
Owner John Brescio utilized his years of experience in the restaurant industry and started the business, wishing to welcome the community to his family’s table.
As the Executive Chef, Brescio creates simple and focused dishes, highlighting local ingredients and the sumptuous seafood around the area.
The menu at Liv’s evolves with the seasons to give guests a taste of the changing environment on the Connecticut coast.
As you enter, you are met with a gorgeous mural of the coast and the sight of the brick dining room resplendent with pristine mirrors, chandeliers, and tablecloths.
Try out starters like Ahi tuna poke and red wine poached mussels, classic main courses like sesame salmon or shrimp and cod curry, and of course, six types of delicious oysters on the half shell.
Watch a Show at the Katharine Hepburn Cultural Arts Center
Actress Katharine Hepburn moved to Old Saybrook’s borough of Fenwick Inn in 1912.
She would continually return to her family homestead throughout her life, eventually choosing to retire there in 1997.
In 2009, the museum and theatre were opened to honor her, a Colonial Revival building with a Doric portico located in the 1911 historic former town hall on Main Street.
Known locally as The Kate, the Center is a non-profit performing arts organization that stands for Katharine Hepburn’s long-lasting legacy.
Here, see a small museum with items like rare photographs from her life and career, contemporary movie posters, her very own self-portrait, and her Emmy award.
The charming 250-seat theatre offers a host of performing arts productions in comedy, dance, film, music, opera, and children’s programming.
You can also catch famous singers and small-town bands who grace the place with their performances.
Hang Out at Monkey Farm Café
Monkey Farm Café is found in Old Saybrook’s historic 1800 Old Stage Inn and is a beloved local hangout and watering hall boasting amazing food.
Here you will find a relaxing barroom ambiance with old exposed beams and dartboards lining the wall.
You can see a game on the TV, play pool with friends, chill on the wraparound porch, or come by for a weekend meal.
A piled-up roast beef sandwich was common at the Inn in the 1960s, though its first focus was serving alcoholic drinks.
In the early 1960s, the innkeeper asked a customer to watch over the Inn, who then famously replied, “They’ll let anyone work here; this place is nothing but a Monkey Farm,” sealing its name.
The menu ranges from classic pub food like pizza, burgers, and sandwiches to delicacies like shrimp scampi, swordfish, and salmon.
Touch Upon History at Fort Saybrook Monument Park
At this park, grab some outdoor time, and have a small history lesson all at once.
Fort Saybrook Monument Park stretches 18 acres near the Connecticut River mouth and is scattered with pieces of history covering the area’s past, from the late 1500s to the Fort’s leveling and transformation.
The park marks the site of a fort created by English military engineer Lion Gardiner to guard the Old Saybrook settlement from scuffles between the Pequot tribe and English settlers.
At the park, one can find a 1930 monument erected in Gardiner’s memory.
The original fort was built in 1635 in honor of Lord Brooke, and Lord Say and Sele, the town’s namesakes to whom these lands were granted.
One can walk to the park to find plenty of markers with information about the fort, the settlement, the nearby river, marshlands, and trek boardwalks to see coastal birds and wildlife.
Stay the Night at Saybrook Point Resort and Marina
Tucked amid Long Island Sound and the Connecticut River, Saybrook Point Resort and Marina prides itself on its serene waterfront setting.
If you’re looking to lap up some luxury for a night or two, this entrancing hotel is the place to be, with its unparalleled views, 82 comfortable rooms, large historic guesthouses, and a lavish spa.
The hotel’s Lighthouse Suite was dubbed the “most romantic place to stay” with its views of the beautiful vistas on the Sound.
Along with world-class amenities, the marina also offers top-quality yacht services, has a full-service marina supply shop, and can accommodate boats from 13 to 140 feet.
One can also delight in dining at Fresh Salt, the elegant upscale restaurant with spectacular views of the Connecticut River and serves fresh American seafood.
The hotel has truly created a perfect balance of northern lavishness and southern hospitality for its eager guests.
Glimpse the Revolution Era at the General William Hart House
The General William Hart House is one of the earliest houses in Saybrook.
It was built in 1767 for politician and colonial military leader William Hart who dedicated it to his bride Esther Buckingham.
An interesting aspect is the many details the building carried that people commonly found in houses in Virginia, Williamsburg, and Dutch Pennsylvania.
The building is a great example of Georgian residential architecture: a 2.5 story wood-frame structure with five bays and a gabled roof, two chimneys, a clapboard exterior, and a central entry framed by a gable-roofed portico and Doric columns.
Inside, visitors will spot memorabilia from different eras, including a sealskin-coated Cromwellian Chair, the Saybrook/Guildford chest, and an intricate outfit belonging to Governor John Winthrop Junior.
Visitors shouldn’t miss the 18th-century style Hart House Heritage Gardens behind the house, blooming with fruit trees, flowers, shrubs, and roses that flourish during summer and spring.
Have Some Tee Time at Fenwick Golf Club
Fenwick Golf Club is on the southeastern tip of Old Saybrook and is open to the public year-round.
It is Connecticut’s oldest golf course and the second oldest public golf course in the state, with the first three holes (5,6,7) finished in 1894 and the 9-hole course completely established in 1896.
The upper level of the 6th green serves as the oldest green in the state of Connecticut in its original location.
The course is on a peninsula at the mouth of the Connecticut River, and from every hole, it provides breathtaking views of the River, Long Island Sound, and the South Cove.
Fenwick’s basic purpose is that golfers of different skill levels can enjoy its strategic, unique link design.
The green speeds, difficult topography, hole designs, and elements all combine to make the course as challenging as possible.
Go Fishing With Reel Cast Charters
For quality Northeastern inshore angling experience, hire Reel Cast Charters, an experienced fishing guide service.
It specializes in the Connecticut waters of Long Island Sound, and it provides a unique service in that they do the bulk of fishing in shallow waters using light tackle.
Reel Cast Charters carved its own niche in Northeastern sports fishing, giving anglers a one-of-a-kind experience in fishing for trophy-sized striped bass with light tackle.
They don’t do any trolling or conventional oversized reels; instead, they do fishing live baits, topwater, and more artificial lures for big fish.
They begin to fish in March on the Housatonic and Connecticut Rivers for holdover and migrating striped bass, and through summer, they target big striped bass on Eastern Connecticut shores.
In the fall, they target surface-feeding false albacore, striped bass, bonito, and bluefish with light spinning and fly rods, and they also have inshore bottom fishing trips for blackish.
Watch the Waves at Harvey’s Beach
No trip to the Connecticut coast is complete without a trip to the beach, and folks often hail Harvey’s Beach as among the best ones on the shoreline.
It is a great spot for swimming in the calm and shallow water, beachcombing on the sand during low tide, taking out a boat to go exploring, and watching an incredible sunset.
There is a dramatic difference between the beach’s size at high tide and low tide; when the water is out, you can walk a long way along the offshore sandbars and even take your chairs out on the dry sand.
For more relaxation, there is a huge pavilion with picnic tables and shade, a free library that offers reading material, and food trucks where you can get desserts.
Occasionally, the town’s parks and recreation department presents fun programs for the public to enjoy, such as beach yoga and movie nights.
Get in Touch with Nature at The Preserve
Old Saybrook holds a 963-acre coastal forest whose vast scope covers a large area of land in the town and in the towns of Westbrook and Essex.
This pristine land was the largest expanse of remaining unprotected coastal forest amid Boston and New York before its acquisition for conservation in 2015.
Since then, it has become a well-loved, protected environment with diverse ecosystems within its acres.
The area includes ponds, vernal pools, canopied woods, freshwater seeps, swamp habitats, mature coastal forest, tributaries or headwaters of the Mud River, Oyster River, and Trout Brook.
This sizable preserve has a variety of flora and fauna: over 30 mammal species, 57 bird types, and 25 amphibian breeds were spotted in the past.
Reptile species were also spotted, such as spotted turtles, box turtles, and northern dusky salamanders.
You can hike on 10 miles of trails teeming with wildlife in the middle and northern preserve.
Take a Ride on the Essex Steam Train and Riverboat
The Essex Steam Train’s 2.5-hour train or riverboat journey begins at the historic 1892 Essex Station for a round trip in the heart of Connecticut River Valley, with a ride ending at Old Saybrook.
The steam locomotive takes visitors through picturesque New England towns of Chester and Deep River, with sweeping nature views of Selden Neck State Park and the tidal wetlands of Chester Creek and Pratt Cove.
The steam train gives passengers an eco-excursion, offering access to many coves and preserves.
These are natural habitats for ducks, swans, cormorants, Greenland geese, blue herons, red-winged blackbirds, and egrets.
During February and March, passengers may glimpse the spectacular bald eagle migrating south from Canada and Maine to the Connecticut River Valley.
And at Deep River Valley, passengers board the Becky Thatcher riverboat to soak up the valley’s natural beauty and see impressive landmarks before embarking on the return train.
Other Things to Do Nearby
Spot Impressionist Works at the Florence Griswold Museum
For anyone cherishing American art, this museum in the town of Old Lyme, 9 minutes from Old Saybrook, is an unmissable stop.
The museum is a yellow Georgian masterpiece designed by Samuel Belcher in 1917, owned by Florence Griswold.
Griswold ran a boarding house in which numerous American Impressionist artists stayed, practicing their craft.
After artist Henry Ward Ranger boarded here, he invited his artist friends, and soon there was a gathering of creatives forming the Old Lyme Art Colony.
Between 1899 and the 1930s, over 130 boarded in this home, some of whom were invited to paint panels on the doors and walls – today almost 41 painted panels are displayed.
The museum is made of a historic house and the Krieble Gallery; here, you can watch a movie telling its story and learn the tales of the artists.
Explore the Outdoors at Rocky Neck State Park
Rocky Neck Park in the town of East Lyme is located 15 minutes from Old Saybrook and is among the most visited state parks in Connecticut.
It is trendy for its beautiful, sloping, soft, sandy beach where one can busy themselves on a summer day, build a sandcastle, make a splash in the water, or spread out a picnic.
Anyone can also try camping in one of its many sites; looking for blue crabs at Baker’s Cave; fishing for flounder, mackerel, and striped bass at Bride Brook; and looking for cranes, herons, ospreys, and other waterfowl around the area.
And one can relax in its 110-meter Rustic-style pavilion, built in the 1930s during the Great Depression.
In its 713 acres, hike through diverse trail systems of varying difficulty, salt marsh platforms, rocky shoreline, a tidal river, a shipyard, and a cave.
There are myriad ways to spend a wonderful day with the family while at Rocky Neck State Park.
Like many of the best towns along the Connecticut shoreline, Old Saybrook is a haven of sandy beaches, natural delights, thriving culture, historical antiquities, culinary adventures, and artistic flourishes.
If you find yourself attracted to this wonderfully scenic town, bring this list to check off the best things you can do here.
The natural beauty of Old Saybrook makes it well worth anyone’s time, and you can start planning to treat yourself to a lovely trip in town.