Things To Do In Old Saybrook CT: Top 21 Most Unique Spots | Stanton House Inn

Beach homes lining the shoreline, walking here is one of the best things to do in Old Saybrook, CT

Old Saybrook is one of Connecticut’s oldest towns. It sits at the meeting point of the Connecticut River and the Long Island Sound. Sandy beaches, outdoor patios, and grand old mansions evoke the vibe of Old Saybrook. It’s family-friendly, and a perfect escape a little over 100 miles (either way) on the New York City to Boston drive.


There’s plenty more to do than enjoy a summer beach day, though. Old Saybrook hosts arts and crafts shows, boat shows, and sidewalk sales. You can find fireworks displays, outdoor concerts, carol singing, and theatrical works.


Thinking about a day trip or a weekend getaway? Old Saybrook offers stunning water views and a palpable historical charm. It’s a place where the past and present mingle on every street corner. It’s a hidden gem, exuding old-world charm and New England hospitality.


Ready to explore the best things to do in Old Saybrook, CT? Let’s get into it:


Quick hits

  • Explore Old Saybrook, CT’s captivating history and outdoor activities
  • Discover unique attractions like Main Street, The Kate theater & Fort Griswold Monument Park
  • Enjoy delicious seafood dishes at Liv’s Oyster Bar & Restaurant or stay in luxury with a visit to the Saybrook Point Resort & Marina

things to do in old saybrook ct map Things to Do in Old Saybrook CT: Top 21 Most Unique Spots
Map design by Stanton House Inn

A Brief History of Old Saybrook, Connecticut

Postcard of the Outer Light, from between 1930 and 1945

The story of Old Saybrook begins with John Winthrop the Younger, who founded the Saybrook Colony in 1635. This colony was strategically located at the mouth of the Connecticut River. It housed a short-lived factory and trading post known as Kievits Hoek. Only three years prior, in 1633, Fort Goede Hoop had been established in what is now Hartford.


Early Colonial Period

The Saybrook Colony was established in late 1635. John Winthrop, the Younger, served as its governor.


The Pequot War was a tumultuous time for the fledgling colony. The Pequot retaliated against the settlers, leading to over 20 casualties at the Saybrook Fort. Both sides assessed each other’s military capabilities, leading to the Pequot War in the Connecticut Colony. This conflict indirectly resulted in the attack and destruction of Mistick Fort.


The colony faced additional challenges, as its principals were supporters of Oliver Cromwell and remained in England during the English Civil War. In 1644, Colonel George Fenwick merged the struggling colony with the more prosperous Connecticut Colony.


The Flag of Connecticut originated from the seal of Saybrook Colony. It depicted 15 grapevines and a hand in the upper left corner with a scroll reading “Qui Transtulit Sustinet,” which translates to “He who transplanted sustains.” In 1647, Major John Mason assumed command of Saybrook Fort, which controlled the main trade and supply route to the upper river valley. The original fort was destroyed by a fire, but a new, improved fort was built nearby.


In 1661, a witch trial was conducted against Saybrook residents Margaret Jennings and her husband Nicholas. They were accused of causing the deaths of Marie Marvin and others. The trial concluded that they were likely witches, but there wasn’t enough evidence to execute them.


The Collegiate School of Connecticut

Circa 1930-1945 postcard of Chalker Beach

The Collegiate School of Connecticut was chartered in Old Saybrook in 1701. It later moved to New Haven, Connecticut, in 1716 and was renamed Yale University.


Katharine Hepburn

Old Saybrook’s most famous resident, Katharine Hepburn, spent her final years at her family’s cherished summer home here. This home in the Fenwick borough, a long, white-brick house, overlooks the Long Island Sound where Ms. Hepburn loved to swim. The house was rebuilt in 1939. The original, built around 1870, was destroyed in the 1938 hurricane. In her memoir, “Me: Stories of My Life,” Ms. Hepburn shared her escape from the storm. She climbed out the dining room window and watched her home “just sail away.”


And on June 29, 2003, Katharine Hepburn, the celebrated film star, passed away here. She was 96.


The Best Things to do in Old Saybrook, CT

Lynde Point Lighthouse

Present day Old Saybrook is a quiet town. But, it’s more than meets the eye. People from different walks of life are drawn here, each finding something unique to love.


Main Street is the heart of the town. It’s alive with shopping and dining. It’s also an ideal spot to soak in the local ambiance.


But, Old Saybrook isn’t just about Main Street. There are other attractions too. Each offers a unique experience, showcasing the town’s diversity.


Take the Saybrook Point Resort, for example. It’s a popular dining spot. And Mini Golf at Saybrook Point is quite the attraction. It opens on Memorial Day weekend and stays that way until Columbus Day Weekend. And the best part? You don’t even need to be a guest here to enjoy it.


Then there are local dining favorites like Skippers Seafood and Monkey Farm Cafe.


Main Street

Historic home in one of Connecticut's oldest towns | Elisa.rolle, CC BY-SA 4.0 <>, via Wikimedia Commons
Elisa.rolle, CC BY-SA 4.0, via Wikimedia Commons

As is typical of New England villages, Main Street embodies the spirit of Old Saybrook. A delightful fusion of the old and new, historic buildings house contemporary businesses. This street is perfect for a leisurely stroll, shopping in local shops, and soaking up the historic ambiance.


The variety of shops on Main Street offer a unique shopping experience. From Cottage Flair’s country-style home decor to Harbor Books’ diverse book collection, there’s sure to be something for you. Adding to its charm, Main Street is also great for a casual bike ride.


Katharine Hepburn Cultural Arts Center

The Katharine Hepburn Cultural Arts Center, also known as “The Kate”, is a tribute to Old Saybrook’s most famous resident, Katharine Hepburn. This popular venue hosts performances and events. It also houses a museum dedicated to Hepburn’s life and career. The museum offers a deep dive into the actress’s life through a compelling display of items.


  • photos
  • movie posters
  • a self-portrait
  • an Emmy award she won

And all in a building on the National Register of Historic Places. If you’re a fan of the actress, or simply love arts and culture, you’ll find The Kate offers a rewarding experience that you won’t want to miss.


General William Hart House

Yale University was founded in 1701 in Old Saybrook, Connecticut, at the salt box-style Buckingham House.

And speaking of historic places, The General William Hart House attests to Old Saybrook’s rich history. This historic Georgian colonial house, dating back to 1767, is now home to the Old Saybrook Historical Society. Here, history enthusiasts can immerse themselves in the past, learning about the town’s early days and its significant historical figures like General William Hart.


The house, along with its 18th-century-style gardens, serves as a window to the past, offering a glimpse of Old Saybrook’s historical charm.


Parks in Old Saybrook, Connecticut

Old Saybrook is a town steeped in history, but it also shines with its impressive collection of parks. These natural spaces offer visitors opportunities to explore the outdoors, participate in recreational activities, or simply unwind amidst the scenic beauty. Each park presents a unique experience, ranging from historical sites to beachfront paradises.


Fort Saybrook Monument Park

Print of Saybrook Fort in 1636

Fort Saybrook Monument Park is a great place to enjoy the outdoors and learn some history.


The park stretches over 18 acres near the mouth of the Connecticut River. It’s full of historical remnants that date back to the late 1500s.


The park stands on the site of an old fort. The fort was designed by Lion Gardiner, an English military engineer. He built it to protect the Old Saybrook settlement during conflicts between the Pequot tribe and English settlers. You can find a monument to Gardiner, erected in 1930.


The original fort, built in 1635, was named in honor of Lord Brooke, and Lord Say and Sele. These were the town’s namesakes who were granted these lands.


The park is also an educational site. Informational markers about the fort, the settlement, the nearby Connecticut River, and marshlands are scattered throughout. Boardwalks provide opportunities to spot coastal birds and wildlife.


Fort Griswold Monument Park

Step back in time at the original site of the Saybrook Colony founded in 1635. Today, the park serves as a reminder of the town’s rich heritage. It also features remains of the Connecticut Valley Railroad’s roundhouse and turntable.


Beyond its historical importance, the park also provides a tranquil backdrop for a relaxed walk, with boardwalks winding through the riverside salt marsh.


Harvey’s Beach

Harvey's Beach in Old Saybrook

For beach lovers, a visit to Old Saybrook is incomplete without a stop at Harvey’s Beach. This family-friendly beach is one of the best beaches in CT, offering:


  • Soft white sand
  • Calm shallow waters
  • Lifeguards
  • Restrooms
  • Concession stand


Whether you aim to bask in the sun, construct sandcastles, or just relish the sound of the waves, Harvey’s Beach is an ideal place to relax and appreciate the beauty of the Connecticut coastline.


The Preserve

For nature enthusiasts, a visit to The Preserve in Old Saybrook is a must. This 1,000-acre coastal forest is an untouched gem. It houses over 57 bird species, 30 mammals, and 25 amphibians and reptiles. The Preserve offers a break from the daily grind, perfect for nature aficionados and outdoor adventurers.


Once, it was the largest remaining area of unprotected coastal forest between Boston and New York. Today, it’s a haven of densely canopied forest, freshwater seeps, wetlands, and ponds. The Preserve is home to a diverse wildlife population including over 57 bird species, 30 mammals, and 25 amphibians and reptiles.


Multiple CT hiking trails guide visitors past the Oyster River and the Mud and Trout Brook Rivers, tributaries of the Long Island Sound. Parking is available at 1278 Essex Road in Westbrook, CT, and five spaces on Ingham Hill Road in Old Saybrook.


South Cove Wildlife Area

Last but not least, the South Cove Wildlife Area is another nature lover’s paradise. This protected natural habitat is home to a variety of wildlife, making it an ideal spot for birdwatching and nature photography. With its calm environment and plentiful natural splendor, South Cove Wildlife Area provides an ideal conclusion to your Old Saybrook adventure.


Lynde Point Lighthouse

Lynde Point Lighthouse

The Lynde Point Lighthouse remains a beacon of Old Saybrook’s maritime history. This historic attraction offers breathtaking views of the coastline, making it a popular spot for photography and sightseeing. Though this Connecticut lighthouse is private property, its beauty can be appreciated from afar, especially from the water.


Myrcene Ale Co

Pouring an ale at a brewery near Saybrook Point, where the Connecticut River meets Long Island Sound

For craft beer enthusiasts, a visit to Myrcene Ale Co is a must. This family and dog-friendly brewery offers a unique selection of brews, often hosting food trucks for a complete food and drink experience.


With its friendly ambiance and premium brews, Myrcene Ale Co is an excellent place to relax following a day of discovering Old Saybrook. It’s one of the best breweries in Connecticut, after all.


Seasonal Celebrations: Annual Events in Old Saybrook

Old Saybrook is a town where history and nature coexist beautifully. But it’s not just about the structures and landscapes. This town is also a hub for annual celebrations and gatherings. Each year, events like the Taste-of-Saybrook Fest and boat shows light up the town. Other festivities include the Fall and Halloween Festival at Westbrook Outlets, arts and craft shows, and sidewalk sales. Music fills the air during the Summer Pops Concert and weekly outdoor concerts on the town green. Old Saybrook is a place that knows how to celebrate.


Shopping in Old Saybrook, Connecticut

historic register in an antique shop in one of Connecticut's oldest towns

The town’s charm extends to its shopping scene too. Old Saybrook offers a unique shopping experience, with numerous antique stores and unique boutiques just waiting to be explored.


Two of the town’s shopping highlights present an array of unique discoveries for the selective shopper.


Essex Saybrook Antiques Village

At Essex Saybrook Antiques Village, you’ll find an array of antiques and vintage items that tell stories of times gone by. This antique store, housed in a barn built around 1850, offers a unique shopping experience, with its charming atmosphere and wide selection of antiques.


Tova’s Vintage Shop

Another shopping gem in Old Saybrook is Tova’s Vintage Shop. This unique boutique offers an assortment of vintage items, including clothing, jewelry, and accessories. With its curated selection of vintage finds, Tova’s Vintage Shop is a must-visit for anyone seeking one-of-a-kind items.


Restaurants in Old Saybrook, CT

Dining on a rainy day in Old Saybrook

Old Saybrook’s charm extends to its culinary scene as well. The town offers a variety of dining options, ranging from upscale seafood restaurants to cozy pubs and cafes.


Liv’s Oyster Bar & Restaurant

Right on Main Street, Liv’s Oyster Bar & Restaurant offers a dining experience like no other. The restaurant serves delicious seafood-centric dishes using fresh local ingredients. From Oysters Rockefeller to Pan-Seared Scallops, each dish is a culinary masterpiece that will tantalize your taste buds.


Penny Lane Pub

Breakwater Light

For a taste of traditional English pub fare, head to Penny Lane Pub. This English-style pub offers a cozy ambiance, complete with rich, dark wood decor and black leather booths. It’s the perfect spot to enjoy a hearty meal, a pint of beer, and some live entertainment on the weekends.


From Fish and Chips to Shepherd’s Pie, the pub’s menu features classic English dishes that are sure to please your palate.


Monkey Farm Cafe

If comfort food is what you crave, Monkey Farm Cafe in Old Saybrook, CT is the place to be. This popular cafe serves up delicious dishes in a cozy setting. From soups and sandwiches to pizza, the menu offers a wide variety of options from which to choose.


Johnny Ad’s

For a casual dining experience, head to Johnny Ad’s. This restaurant offers a range of American comfort food like:

  • burgers
  • sandwiches
  • seafood
  • and more


Whether you’re a foodie or just looking for a tasty meal, Johnny Ad’s is a great choice.


With its delicious food, friendly service, and relaxed atmosphere, it’s no wonder Johnny Ad’s has become a favorite among locals and visitors alike.


Directions to Old Saybrook, CT, from Greenwich, CT

Picnic bench along the Connecticut River and Long Island Sound

Getting to Old Saybrook from our Greenwich, CT, bed and breakfast is quite straightforward. You can take the I-95 N from Greenwich, Connecticut, to Old Saybrook. The journey is approximately 50 miles and takes about an hour and a half, depending on traffic.


If you prefer train trips from NYC or Greenwich, you can take the Metro-North train from Greenwich to New Haven, and then transfer to the Shore Line East train to Old Saybrook.


Hotels, Inns, and Places to Stay in Old Saybrook, Connecticut

Hotel room at Saybrook Point Resort

Or stick around for longer, if you like. One standout for its opulence and exceptional service is the Saybrook Point Resort & Marina. It provides a distinctive mix of comfort and sophistication, making it a leading choice for travelers desiring a remarkable stay in Old Saybrook.


Saybrook Point Resort & Marina

One of the fishing charters, pursuing blue crabs in Long Island Sound

Saybrook Point Resort & Marina sits in Old Saybrook, offering luxury and stunning views of the Connecticut River and Long Island Sound. The resort features 82 rooms in its Main Inn. It also owns two historic guesthouses across the street. After a day of exploration, the spa offers a luxurious retreat. For dining, Fresh Salt serves delectable meals on the outdoor patio. The resort also boasts a world-class marina, accommodating yachts of all sizes. For an unforgettable experience, guests can choose the Lighthouse Suite. This unique suite, located on the main dock, offers stunning vistas of the Sound. It has been dubbed one of the most romantic places to stay in CT. Each room at the resort is stylishly furnished. They come with private balconies, complimentary wifi, and iHome radios.


If you’d like to stay in a Connecticut shoreline bed and breakfast, head next door. The town of Westbrook, Connecticut, is home to two fantastic bed and breakfasts, across the road from each other:

  • The Westbrook Inn bed and breakfast
  • The Captain Stannard House bed and breakfast


More Towns and Cities to Explore Near Old Saybrook, Connecticut

Birds along the shore at Rocky Neck State Park in East Lyme, CT

While Old Saybrook is a destination on its own, it’s also surrounded by towns and cities that merit a visit. Each of these Connecticut places possesses its distinct appeal and attractions.


The beautiful Connecticut shoreline along Long Island Sound offers a breathtaking view and a perfect getaway for tourists and locals alike. The Connecticut Valley Railroad, running parallel to the shoreline, adds to the charm of this picturesque region in Middlesex County.


Essex, CT

Historic home in Essex village

Essex is known for its arts and craft shows, boat shows, and the Taste-of-Saybrook Fest. The charming Essex town is famous for its historical significance and vibrant arts scene. Here, you can visit such Essex, CT, attractions as the Connecticut River Museum, Essex Steam Train and Riverboat, and the Pratt House. The town also hosts various events throughout the year, such as the Annual Arts & Crafts Festival, making it a vibrant destination for art lovers and history buffs alike.


Old Lyme, Connecticut

Old Lyme is home to the Midsummer Festival and the Lyme Art Association. The town of Old Lyme, CT, is picturesque, and played a significant role in the development of American Impressionism. It’s home to the Florence Griswold Museum, a former artist colony and boarding house run by Florence Griswold. Black Hall Outfitters and the Sculpture Grounds attract visitors as well.


Whether you’re an art enthusiast or a nature lover, Old Lyme offers a unique blend of culture and natural beauty that’s sure to captivate you, just like it did the renowned Lyme Art Colony.


East Lyme, CT

East Lyme, CT, is a town that offers a variety of attractions for visitors of all ages. Here, you can visit Niantic Bay Boardwalk, Rocky Neck State Park, and the Children’s Museum of Southeastern Connecticut in the seaside borough of Niantic, CT.


East Haddam, Connecticut

Church in East Haddam, one of the most popular places to visit near the town of Old Saybrook

Last but not least, East Haddam, Connecticut, is a town worth exploring. Known for its historical significance and natural beauty, East Haddam is home to attractions like Gillette Castle State Park and Devil’s Hopyard State Park. If you’re a history buff or a nature enthusiast, East Haddam offers a unique blend of the past and the present that’s sure to captivate you.



Old Saybrook, Connecticut, is a town that exudes charm. Its rich history and vibrant cultural scene make it a unique destination. The blend of New England hospitality and coastal beauty is truly captivating. Whether you’re interested in history, nature, food, or shopping, Old Saybrook has something to offer. Plan one of the best day trips in CT and experience the allure of this coastal gem yourself.


Frequently Asked Questions

Breakwater Light

Does Old Saybrook have a downtown?

Yes, Old Saybrook has a charming downtown that has served as the setting for numerous Hollywood movies.


Does Old Saybrook have a beach?

Yes, Old Saybrook does have a beach! It’s called Harvey’s Beach. Spanning about 100 yards, this beach offers a variety of amenities. These include lifeguards, a concession stand, a playground, ample parking, and changing rooms.


What is it like to live in Old Saybrook CT?

Old Saybrook is a quaint, rural town known for its picturesque scenery. Its iconic Main Street, dotted with unique shops and restaurants, exudes a classic New England charm. The residents, predominantly well-educated and politically liberal, take pride in their highly-rated public schools. Old Saybrook’s central location along Interstate 95 also provides easy access to nearby destinations.


What is the oldest house in Old Saybrook?

The Elisha Bushnell House, located on the Boston Post Road in Old Saybrook, is the oldest house in town. It was built in 1678 by The Elder Joshua Bushnell and has survived through centuries as one of the five oldest houses in Connecticut.


What’s the best time to visit Old Saybrook?

Summer is the best time to visit Old Saybrook. The warm weather and range of outdoor activities make it the perfect destination for your next vacation.


Leave a Reply

Your email address will not be published. Required fields are marked *