Top-Rated Things to Do in Old Saybrook, CT

Connecticut

By Omar Perez

Welcome to Old Saybrook, a charming coastal town in Connecticut that offers a wide range of activities for visitors of all ages. Located at the mouth of the Connecticut River, Old Saybrook boasts picturesque views, historical landmarks, and a vibrant arts and culture scene. Whether you’re a nature enthusiast, a history buff, or simply looking to relax by the shore, Old Saybrook has something for everyone.

If you’re a fan of outdoor activities, you won’t be disappointed in Old Saybrook. Take a stroll along the town’s beautiful Main Street, lined with unique shops, galleries, and restaurants. Or head to one of the nearby beaches to enjoy a day of sun, surf, and sand. The town is also home to several nature preserves and parks, where you can hike, bike, and birdwatch to your heart’s content.

For history lovers, a visit to the General William Hart House is a must. Built in 1767, this historic home offers a glimpse into the past with its period furnishings and artifacts. Another popular historical site is the Saybrook Point Inn and Spa, which was once a military fort and now serves as a luxurious resort and spa. Don’t miss the opportunity to explore the area’s rich maritime heritage at the Connecticut River Museum, where you can learn about the region’s shipbuilding and maritime commerce.

Art and culture enthusiasts will feel right at home in Old Saybrook. The Katharine Hepburn Cultural Arts Center, also known as “The Kate,” is a vibrant venue that hosts a variety of performances, from live music and theater to film screenings. The Old Saybrook Art Center showcases the work of local artists and offers classes and workshops for those looking to unleash their own creativity. And for a dose of nostalgia, be sure to catch a movie at the charming Old Saybrook Drive-In Theatre.

With its beautiful scenery, rich history, and vibrant arts scene, Old Saybrook is a hidden gem that is not to be missed. Whether you’re planning a weekend getaway or a longer stay, this coastal town has something for everyone. So come and experience all that Old Saybrook, CT has to offer!

Discover Historic Sites

Old Saybrook, CT is a town rich in history, with numerous historic sites to explore. Whether you are a history buff or simply interested in learning more about this charming town’s past, there are plenty of must-see sites to visit. Here are some of the top-rated historic sites in Old Saybrook:

Saybrook Point

Located at the mouth of the Connecticut River, Saybrook Point is the site of the original settlement of Old Saybrook in 1635. It is home to several historic buildings, including the Saybrook Point Lighthouse, which dates back to 1886. Visitors can tour the lighthouse and learn about its fascinating history.

The General William Hart House

Built in 1771, the General William Hart House is a well-preserved example of Federal style architecture. It was the home of General William Hart, a prominent figure in the Revolutionary War. Visitors can tour the house and view furnishings and artifacts dating back to the 18th century.

The Katharine Hepburn Cultural Arts Center

Located in a former town hall building, The Katharine Hepburn Cultural Arts Center is named after the famous actress and Old Saybrook resident. The center hosts a variety of performances, exhibits, and educational programs throughout the year. Visitors can enjoy live theater, music concerts, art exhibits, and more.

The Gen. William Tryon House

Built in 1710, the Gen. William Tryon House is a historic home that once belonged to Governor William Tryon of the Province of New York. Today, it serves as a museum and art gallery, showcasing regional artwork and artifacts from the colonial era. Visitors can explore the house and learn about its rich history.

The Old Saybrook Historical Society

The Old Saybrook Historical Society operates several historic properties in the town, including the Hart House and the Gen. William Tryon House. The society offers guided tours and educational programs, providing visitors with a deeper understanding of Old Saybrook’s history. It also hosts special events and exhibits throughout the year.

Exploring Old Saybrook’s historic sites is a great way to immerse yourself in the town’s rich heritage and learn more about its fascinating past. Whether you are interested in architecture, art, or local history, there is something for everyone to discover in this charming Connecticut town.

Explore Saybrook Point

Saybrook Point is a picturesque waterfront area in Old Saybrook, CT that offers a variety of activities for visitors to enjoy. Situated at the mouth of the Connecticut River, this scenic destination is perfect for outdoor enthusiasts, history buffs, and food lovers alike.

One of the highlights of Saybrook Point is Saybrook Breakwater Light, also known as Saybrook Outer Light. This historic lighthouse is located at the end of a half-mile long stone jetty and dates back to 1886. Visitors can take a leisurely stroll along the jetty and admire the iconic lighthouse, which is a popular spot for photographers.

In addition to the lighthouse, Saybrook Point also offers beautiful beaches where visitors can relax and soak up the sun. With its sandy shores and calm waters, it’s a great place for swimming, beachcombing, and picnicking. Beach chairs, umbrellas, and other beach amenities are available for rent.

If you’re looking for a bit of adventure, Saybrook Point offers kayak and paddleboard rentals. Explore the scenic Connecticut River estuary and see the local wildlife up close. Guided tours are also available for those who want to learn more about the history and ecology of the area.

After a day of exploring, visitors can relax and enjoy a meal at one of the waterfront restaurants at Saybrook Point. From fresh seafood to gourmet cuisine, there is something to satisfy every palate. Many of the restaurants offer outdoor seating with stunning views of the river and marina.

For those interested in history, a visit to the Old Saybrook Historical Society is a must. Located near Saybrook Point, this small museum showcases the rich history of the area through exhibits and artifacts. Learn about the Native American tribes who originally inhabited the region, the arrival of European settlers, and the development of Old Saybrook into a bustling port town.

Whether you’re seeking relaxation, adventure, or a taste of history, Saybrook Point has something for everyone. Plan your visit today and discover all that this charming waterfront area has to offer.

Visit the Katharine Hepburn Cultural Arts Center

The Katharine Hepburn Cultural Arts Center, also known as “The Kate,” is a historic theater located in Old Saybrook, Connecticut. Named after the legendary actress Katharine Hepburn, the center is dedicated to promoting the arts and inspiring creativity in the community.

Opened in 2009, The Kate features a variety of performances including live theater productions, musical concerts, and film screenings. The venue has a seating capacity of 250 and offers an intimate setting for audiences to enjoy world-class entertainment.

The center also offers educational programs and workshops for children and adults, allowing individuals to explore their artistic talents and foster a love for the arts. Additionally, The Kate hosts art exhibits, providing a platform for local artists to showcase their work.

Aside from its cultural offerings, The Kate has a rich history as well. The building that houses the center was originally built in 1911 as a meeting place for the local Woman’s Club. It has since undergone renovations to restore its architectural beauty and preserve its historical significance.

Visitors to The Kate can expect to be transported back in time as they enter the theater. The grand lobby features stunning artwork and photographs of Katharine Hepburn, paying homage to the actress and her impact on the world of entertainment.

Whether you’re a fan of the arts, a history buff, or simply looking for a unique and inspiring experience, a visit to The Katharine Hepburn Cultural Arts Center is a must-do when in Old Saybrook, CT.

Go Shopping on Main Street

One of the top things to do in Old Saybrook, CT is to go shopping on Main Street. This charming street is lined with a variety of unique shops and boutiques that offer a wide range of products.

Whether you’re looking for fashion, home decor, antiques, or specialty food items, you’ll find it all on Main Street. The shops here pride themselves on offering high-quality, one-of-a-kind products that you won’t find anywhere else.

Take a stroll down Main Street and explore the different shops at your leisure. Stop by the clothing stores and browse the latest trends in fashion. You might even find a boutique that offers locally made clothing and accessories.

If you’re in the mood for some home decor, check out the home goods stores on Main Street. From antique furniture to modern pieces, you’re sure to find something that suits your style.

No shopping trip is complete without some delicious treats. Main Street has several specialty food stores where you can find unique gourmet items, artisanal cheeses, locally made jams and jellies, and much more.

Make sure to save some time for a coffee break or a meal at one of the many cafes and restaurants on Main Street. You can refuel and relax while enjoying the local cuisine and soaking in the charming atmosphere of the street.

So, if you’re visiting Old Saybrook, CT, don’t miss the opportunity to go shopping on Main Street. It’s a delightful experience that combines the joy of shopping with the charm of a historic New England town.

Relax on Saybrook Beach

One of the top-rated things to do in Old Saybrook is to relax on Saybrook Beach. This picturesque beach is the perfect place to unwind and enjoy the natural beauty of the area. With its soft sand and gentle waves, Saybrook Beach provides a serene and peaceful atmosphere for visitors.

Whether you’re looking to soak up the sun, take a leisurely stroll along the shoreline, or simply sit and listen to the calming sound of the waves, Saybrook Beach has something for everyone. You can spread out a blanket and have a picnic, build sandcastles with the kids, or go for a refreshing swim in the crystal-clear waters.

For those seeking a bit of adventure, Saybrook Beach also offers opportunities for kayaking and paddleboarding. Renting equipment is easy, and the calm waters make it a great spot for beginners to try out these water sports.

Aside from its natural beauty, Saybrook Beach also boasts some amazing views. From the beach, you can see the Connecticut River flowing into the Long Island Sound, creating a stunning backdrop for relaxation.

Remember to bring along some beach essentials such as sunscreen, a beach towel, and plenty of water to stay hydrated. Saybrook Beach provides ample parking, restrooms, and lifeguards on duty, ensuring a safe and enjoyable experience for all visitors.

So if you’re looking to escape the hustle and bustle of everyday life, head to Saybrook Beach in Old Saybrook and let the soothing waves wash away your worries. It’s the perfect place to relax and recharge while enjoying the beauty of the Connecticut shoreline.

Enjoy Outdoor Activities at Harvey’s Beach

If you’re looking for some fun in the sun, head over to Harvey’s Beach in Old Saybrook. This beautiful sandy beach offers a wide range of outdoor activities for people of all ages.

One of the most popular activities at Harvey’s Beach is swimming. The clean, clear water is perfect for taking a refreshing dip on a hot summer day. Lifeguards are on duty, ensuring that everyone stays safe while enjoying the water.

If you prefer to stay dry, you can relax on the sandy shore and soak up the sun. Bring along a beach towel, a good book, and some snacks, and spend a lazy afternoon enjoying the picturesque views. The beach also has picnic tables and grills, making it the perfect spot for a family barbecue.

In addition to swimming and sunbathing, Harvey’s Beach offers ample opportunities for watersports. You can rent paddleboards, kayaks, and jet skis from various vendors near the beach. Explore the calm waters of Long Island Sound, or try your hand at stand-up paddleboarding for a fun and challenging workout.

If you’re a fishing enthusiast, Harvey’s Beach is also a great spot to cast your line. With its proximity to the ocean, you have a good chance of catching some impressive fish. Whether you’re a beginner or an experienced angler, the beach provides a peaceful and scenic backdrop for a day of fishing.

Whether you’re looking for relaxation or adventure, Harvey’s Beach has something for everyone. Pack your sunscreen and beach gear, and get ready to enjoy a day of outdoor fun in beautiful Old Saybrook, CT.

Take a Boat Tour on the Connecticut River

If you’re looking for a unique and scenic way to explore Old Saybrook, CT, why not take a boat tour on the Connecticut River? This picturesque river offers stunning views and a variety of wildlife to observe.

There are several local companies that offer boat tours, giving you the opportunity to sit back, relax, and take in the beauty of the surrounding area. Whether you’re interested in a leisurely cruise or a more adventurous excursion, there are options for every preference.

During the boat tour, you’ll have the chance to see historic sites, stunning waterfront homes, and even catch a glimpse of some of the diverse bird species that call the Connecticut River home. It’s a great way to learn about the history and natural beauty of the area while enjoying a peaceful and enjoyable experience.

Some boat tours also offer the opportunity to disembark and explore nearby attractions, such as Gillette Castle State Park or the Essex Steam Train and Riverboat. This allows you to make the most of your time in Old Saybrook and see even more of what the area has to offer.

Whether you’re a local resident or visiting from out of town, a boat tour on the Connecticut River is a must-do activity in Old Saybrook. So grab your camera, put on your sun hat, and get ready for a memorable and scenic adventure on the picturesque Connecticut River!

Dine at Local Restaurants

When visiting Old Saybrook, CT, don’t miss out on the opportunity to dine at some of the best local restaurants in town. From seafood to Italian cuisine, there is something to satisfy every palate.

One highly recommended restaurant is Café Florentine, which offers a cozy atmosphere and a menu filled with delicious Italian dishes. Whether you’re in the mood for pasta, pizza, or seafood, you won’t be disappointed with the authentic flavors and homemade sauces.

If you’re craving seafood, head over to Liv’s Oyster Bar. This popular spot is known for its fresh seafood dishes and oysters on the half shell. With its nautical decor and waterfront views, Liv’s Oyster Bar provides a true New England dining experience.

For those looking for a taste of local flavors, try The Penny Lane Pub. This charming pub offers a variety of traditional pub fare, such as fish and chips, as well as hearty sandwiches and burgers. Pair your meal with a cold pint of beer and enjoy the cozy atmosphere.

If you’re in the mood for something sweet, make sure to stop by The Tea Kettle. This quaint tea room and bakery offers an array of delectable pastries, cakes, and scones. With its charming decor and friendly staff, The Tea Kettle is the perfect place to indulge in a sweet treat.

Whether you’re a foodie or simply looking for a good meal, Old Saybrook’s local restaurants have something for everyone. Don’t miss the opportunity to explore the culinary delights of this charming town.

Restaurant Cuisine Highlights
Café Florentine Italian Authentic flavors, cozy atmosphere
Liv’s Oyster Bar Seafood Fresh seafood, waterfront views
The Penny Lane Pub Pub Fare Traditional pub food, cozy atmosphere
The Tea Kettle Bakery Delicious pastries, charming tea room

Try Fresh Seafood at Liv’s Oyster Bar

If you’re looking for a taste of the ocean in Old Saybrook, head to Liv’s Oyster Bar. This highly-rated restaurant is known for its fresh seafood and charming atmosphere.

At Liv’s Oyster Bar, you can enjoy a variety of dishes made from locally sourced ingredients. The menu features an array of choices, including a raw bar with a selection of oysters, clams, and shrimp. These tasty treats are shucked to order, ensuring the utmost freshness.

In addition to the raw bar, Liv’s Oyster Bar offers a range of cooked seafood options. From delicious lobster rolls to perfectly seared scallops, there’s something for every seafood lover. The chef at Liv’s creates artful presentations that are as pleasing to the eye as they are to the palate.

Pair your meal with a refreshing cocktail or a glass of wine from their extensive drink menu. The knowledgeable staff can recommend the perfect pairing to complement your chosen dish.

With its friendly service, relaxed ambiance, and incredible seafood, Liv’s Oyster Bar is a must-visit spot for any seafood enthusiast visiting Old Saybrook. So don’t miss out on the chance to tantalize your taste buds with the freshest catch from the Connecticut shoreline.

Indulge in Italian Cuisine at Alforno Trattoria

When it comes to Italian cuisine in Old Saybrook, CT, Alforno Trattoria is a must-visit restaurant. Located in the heart of the town, this charming Italian eatery has been serving up authentic Italian dishes since 1992.

At Alforno Trattoria, you can expect to find a menu brimming with classic Italian favorites. Start off your meal with an appetizer like bruschetta or calamari, or try one of their delicious soups or salads. For the main course, you can choose from a variety of pasta dishes, including lasagna, spaghetti carbonara, and fettuccine Alfredo. They also offer a selection of traditional meat and seafood dishes, such as chicken Parmesan and veal Marsala. And don’t forget to save room for dessert – their tiramisu and cannoli are both highly recommended.

Not only does Alforno Trattoria offer delicious food, but they also provide a warm and inviting atmosphere. The restaurant is decorated with rustic Italian accents, and the friendly staff will make you feel right at home. Whether you’re enjoying a romantic dinner for two or celebrating a special occasion with a group, Alforno Trattoria is the perfect place to indulge in a truly authentic Italian dining experience.

Address 1654 Boston Post Rd, Old Saybrook, CT 06475
Phone (860) 399-4166
Website www.alfornotrattoria.com
Hours
  • Monday-Thursday: 4:30pm-9:00pm
  • Friday-Saturday: 4:30pm-10:00pm
  • Sunday: 4:00pm-9:00pm

Next time you find yourself in Old Saybrook, make sure to visit Alforno Trattoria for a memorable Italian dining experience. With its delicious food, welcoming atmosphere, and exceptional service, it’s no wonder why this restaurant is a top-rated choice among locals and visitors alike.

Savor New England Fare at The Back Porch

If you’re looking for delicious New England cuisine in Old Saybrook, look no further than The Back Porch. This charming restaurant offers a warm and inviting atmosphere, perfect for a casual lunch or a special dinner.

The Back Porch is known for its fresh seafood dishes, including lobster rolls, clam chowder, and grilled fish. But they also offer a wide variety of other options, from juicy steaks to flavorful vegetarian dishes. Their menu features locally sourced ingredients, ensuring each dish is bursting with authentic New England flavors.

Whether you’re a seafood lover or not, The Back Porch has something for everyone. Their menu also includes options like burgers, salads, and sandwiches, all made with the same dedication to quality and taste.

One of the highlights of dining at The Back Porch is their beautiful outdoor patio. Situated just steps away from the Connecticut River, it offers stunning views and a relaxed atmosphere. Enjoy your meal while watching the boats pass by and taking in the natural beauty of the area.

In addition to their delicious food and scenic setting, The Back Porch also offers a carefully curated wine and cocktail menu. Pair your meal with a glass of local wine or try one of their specialty cocktails for a truly memorable dining experience.

With its combination of mouthwatering dishes, inviting ambiance, and picturesque location, The Back Porch is a must-visit for anyone exploring Old Saybrook. Whether you’re a local or just passing through, be sure to stop by and savor the flavors of New England at this delightful restaurant.

Attend Local Events and Festivals

Old Saybrook, CT is known for its vibrant community spirit and offers a variety of local events and festivals throughout the year. Whether you’re interested in music, arts, or food, there’s always something happening in this charming coastal town.

One of the highlights of the year is the Saybrook Stroll, a popular event that takes place in June. During this event, the streets of downtown Old Saybrook are transformed into a lively pedestrian-friendly zone, filled with live music, local vendors, food trucks, and entertainment for the whole family.

If you’re a fan of live music, make sure to check out the Summer Concert Series held at the Katharine Hepburn Cultural Arts Center. This beautiful venue hosts a variety of musicians and performers throughout the summer, showcasing everything from jazz and blues to classical and rock music.

In addition to music events, Old Saybrook also hosts several annual arts and crafts festivals. The Old Saybrook Art Festival is held in July and features works from local artists and artisans. This is a great opportunity to browse and purchase unique handmade items, including paintings, pottery, jewelry, and more.

For food lovers, the Old Saybrook Farmers Market is a must-visit. Held every Saturday from June to October, this market offers a wide selection of fresh local produce, baked goods, artisanal cheeses, and much more. It’s a great place to support local farmers and sample some of the best food the region has to offer.

Whether you’re a resident or just visiting, attending local events and festivals in Old Saybrook is a great way to immerse yourself in the community and experience the unique charm of this coastal town.

FAQs

Can you recommend any good beaches in Old Saybrook?

Yes, there are several beautiful beaches in Old Saybrook. Some popular options include Harvey’s Beach, Old Saybrook Town Beach, and Sound View Beach.

What is the best time to visit Old Saybrook?

The best time to visit Old Saybrook is during the summer months, particularly from June to August, when the weather is warm and you can enjoy the beaches and outdoor activities.

Are there any historical sites to visit in Old Saybrook?

Yes, Old Saybrook is rich in history. Visitors can explore the General William Hart House, which dates back to the 17th century, or visit the nearby Fort Saybrook Monument Park, which commemorates the original fort built in 1635.

What are some popular water activities in Old Saybrook?

Old Saybrook offers a variety of water activities. Visitors can go fishing or boating on the Connecticut River, take a kayak or paddleboard tour, or simply relax on one of the town’s beautiful beaches.

Are there any shopping opportunities in Old Saybrook?

Yes, Old Saybrook boasts a charming downtown area with a variety of shops and boutiques. Visitors can browse local artwork, antiques, and unique gifts at the many stores and galleries.

What are some popular outdoor activities in Old Saybrook?

Old Saybrook has a variety of outdoor activities to offer. Visitors can enjoy swimming, boating, fishing, and bird-watching at Hammonasset Beach State Park. They can also take scenic walks along the town’s many beaches and trails.

Are there any historical sites to visit in Old Saybrook?

Yes, Old Saybrook is rich in history and there are several historical sites to visit. The Saybrook Colony and Museum, which is located on the grounds of Saybrook Point, offers a glimpse into the town’s colonial past. The William Hart House and the Pratt House are two other historical sites worth exploring.

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Omar Perez

Omar Perez, a Caribbean correspondent at TravelAsker, is a skilled writer with a degree from Florida International University. He has published in prestigious outlets like The Miami Herald, Orlando Weekly, Miami Daily Business Review, and various New Times editions. He has also worked as a stringer for The New York Times in Miami, combining his love for travel and storytelling to vividly depict the Caribbean's charm.

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