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Old Saybrook, CT: Where Fun and Adventure Meet! Best Places to Visit and Things to Do

The town runs slow. Old Saybrook sits right on the Long Island Sound and the Connecticut River, and the boardwalk out there goes over a full mile. Rocky Neck State Park carries all of the trails going through the woods and along the shoreline. The Connecticut River Museum runs its own nature trail out through all of the marshes. Nothing here needs booking ahead at all.

You are in for a treat if you are planning a trip to Old Saybrook, Connecticut. This charming town carries a version for everyone, outdoor adventures through to cultural and artistic delights. Travelling with family, friends, or solo, you are sure to find plenty of fun things to do and places to visit in Old Saybrook.

A Glimpse into Old Saybrook’s History Old Saybrook carries a long history that dates back to the 1600s. You can work through this history by visiting the Saybrook Point Inn and Spa, which was once a military fort, or the General William Hart House, which was built in 1767 and is now a museum. You can also take a stroll through the historic district, which is home to many well-preserved colonial-era homes.

Cultural and Artistic Delights Old Saybrook is home to the Katharine Hepburn Cultural Arts Center, which hosts a variety of performances and events throughout the year. You can also visit the Connecticut River Museum to pick up more about the history of the Connecticut River and its role in shaping the town. If you are an art lover, you will not want to miss the Artisans Harbor Gallery, which showcases the work of local artists.

Key Takeaways

• Old Saybrook is a town with a rich history dating back to the 1600s.
• The town is home to a variety of cultural and artistic attractions, including the Katharine Hepburn Cultural Arts Center and the Connecticut River Museum.
• Outdoor enthusiasts will love the many outdoor adventures available in Old Saybrook, from kayaking to hiking.

A Glimpse into Old Saybrook’s History

Ah, Old Saybrook. You might think that this quaint town is only a summer destination, but it carries a long history that dates back to colonial times. In fact, Old Saybrook was one of the original towns in Connecticut, founded way back in 1635 by a group of English Puritans.

One of the more interesting historical sites in Old Saybrook is the General William Hart House. Built in 1767, this house served as the headquarters for General William Hart during the Revolutionary War. Legend has it that General Hart used to hide in a secret room in the house whenever the British were in town. You can take a tour of the house and see the secret room for yourself.

If you are interested in picking up more about the history of Old Saybrook, be sure to stop by the Old Saybrook Historical Society. This organization is dedicated to preserving the town’s history and carries a museum filled with artifacts and exhibits. You can pick up everything from the town’s maritime history to its role in the Revolutionary War.

Another historical site in Old Saybrook that belongs on the list is the Fort Saybrook Monument Park. This park sits on the site of the original fort that was built in 1635 to protect the town from attacks by the Pequot Indians. The fort was destroyed in 1647, but the park carries a monument that commemorates its importance in the town’s history.

So, there you have it. A glimpse into Old Saybrook’s fascinating history. History buff or simply someone after something different to do, be sure to check out these historical sites on your next visit to Old Saybrook.

Cultural and Artistic Delights

Looking for some culture and art in Old Saybrook? You are in luck. This charming town carries a few quiet finds that will satisfy your artistic cravings. Here are the destinations that belong on the list for cultural and artistic delights:

The Kate

If you are a fan of performing arts, you will not want to miss The Katharine Hepburn Cultural Arts Center, also known as The Kate. This historic theater hosts a variety of performances throughout the year, concerts, plays and comedy shows included. The venue is named after the legendary actress Katharine Hepburn, who was born and raised in Connecticut. The Kate is a strong place to catch up-and-coming artists as well as established performers.

Florence Griswold Museum

For a taste of American Impressionist art, head to the Florence Griswold Museum. This charming museum sits in a historic boarding house that was once home to the Lyme Art Colony. The colony was a gathering place for some of the more prominent American Impressionist artists of the early 20th century, Childe Hassam and Willard Metcalf included. The museum’s collection includes over 10,000 works of art, paintings, sculptures and decorative arts included.

If you are a fan of Impressionist art, you will not want to miss the museum’s collection of works by members of the Lyme Art Colony. The museum also hosts rotating exhibitions that showcase a variety of art and artists.

So if you are in the mood for a night of theater or a day of art appreciation, Old Saybrook carries something.

Outdoor Adventures

Looking for some adventure in Old Saybrook? You are in luck. This charming town runs plenty of outdoor activities to keep you occupied. Fishing through to hiking, there is a version for everyone.

Fishing in Old Saybrook

If fishing is your thing, you are in the right place. Old Saybrook sits right on the Long Island Sound and the Connecticut River, which means you carry plenty of chances to reel in some big catches. The town is particularly known for striped bass fishing, so make sure to bring your A-game.

One of the stronger ways to go fishing in Old Saybrook is by booking a charter with Reel Cast Charters. They run half-day and full-day fishing trips that will take you to the stronger spots in the area. Do not worry if you are a beginner, because the experienced crew will help you every step of the way.

If you prefer to fish on your own, head to Saybrook Point or the Town Beach. These spots are popular among locals and visitors alike, so you are sure to have a good time.

Hiking Trails

If you are more of a land lover, Old Saybrook runs plenty of hiking trails for you to work through. Rocky Neck State Park belongs on any hiker’s list. The park carries several trails that will take you through the woods and along the shoreline. Keep an eye out for local wildlife, deer and birds included.

Another strong hiking spot is the Connecticut River Museum. The museum runs a nature trail that will take you through the marshes and wetlands along the river. It is a strong way to pick up the local ecosystem while getting some exercise.

No matter what kind of outdoor adventure you are after, Old Saybrook carries something for you. So grab your fishing rod or hiking boots and get ready for some fun.

Shopping Extravaganza

Looking for a shopping extravaganza in Old Saybrook? You are in luck. This charming town is home to a variety of shops, boutiques and antique stores that are sure to satisfy your shopping cravings. Here are some of the stronger places to check out:

Antique Hunting in Old Saybrook

If you are a fan of all things vintage, then you will love antique hunting in Old Saybrook. Maximus Antiques belongs on the list, with a long selection of unusual and interesting antiques. Furniture through to jewelry, you are sure to find something that catches your eye.

Cottage Flair is another strong option for antique shopping. This cozy shop is filled with a variety of vintage items, home decor, jewelry and clothing included. You never know what you will turn up here.

Main Street Boutiques

For a more modern shopping experience, head to Main Street in Old Saybrook. Here you will find a variety of boutiques and shops, each with their own unusual style.

Saybrook Home is a strong place to start. This home decor store carries everything you need to spruce up your living space, furniture through to accessories. And if you are after something to wear, check out the clothing boutiques on Main Street. You will find everything from casual wear to formal attire.

So if you are in the mood for some antique hunting or a modern shopping spree, Old Saybrook has you covered. Happy shopping.

Culinary Journey

When it comes to food, Old Saybrook carries a version for everyone. Fresh seafood through to craft beer, the town carries a long run of culinary delights that will satisfy your taste buds. Here are some of the leading places you should check out during your visit.

Seafood Delights

Old Saybrook is known for its fresh seafood, and there are plenty of restaurants serving some delicious dishes. If you are in the mood for seafood, head to Fresh Salt. This restaurant sits inside the Saybrook Point Inn and runs long views of the Connecticut River. Their seafood is sourced locally and is always fresh. Make sure to try their lobster roll, because it is one of the stronger ones in town.

Another strong seafood spot is Liv’s Oyster Bar and Restaurant. This restaurant carries a cozy atmosphere and serves some of the stronger oysters in town. If you are not a fan of oysters, do not worry, because they have plenty of other seafood dishes to choose from.

Craft Beer and Wine

If you are a beer or wine lover, Old Saybrook runs some strong options for you. Head to Penny Lane Pub for a pint of craft beer. They have a rotating selection of beers on draught, so there is always something new to try. If you are not sure what to order, the bartenders are always happy to point you at one.

For wine lovers, Sip Wine Bar belongs on the list. They have an extensive wine list carrying wines from around the world. The atmosphere is cozy and intimate, which suits a romantic night out exactly.

If you are after a more casual spot, check out Monkey Farm Café. They have a strong selection of craft beer and wine, as well as delicious food. The atmosphere is laid-back and quirky, which makes it a fun spot to hang out with friends.

No matter what your taste buds are craving, Old Saybrook carries something. Fresh seafood through to craft beer and wine, the town is full of culinary delights that will send you home full.

It goes back. Old Saybrook was one of the original towns in all of Connecticut, founded back in 1635 by a group of English Puritans. The fort itself went up in the same year and then came down again in 1647. The General William Hart House of 1767 still carries its own secret room inside it. Fort Saybrook Monument Park marks where all of it started.

Events and Festivals

Old Saybrook is a town that loves to party, and there are plenty of events and festivals throughout the year to keep you occupied. Outdoor concerts through to sidewalk sales, there is always something going on. Here are some of the stronger events and festivals in Old Saybrook:

• Summer Concert Series: If you love live music, you won’t want to miss the Summer Concert Series. Held at the Old Saybrook Town Green, this series features a variety of musical acts, from rock and roll to jazz. Bring a blanket or lawn chair and enjoy the tunes under the stars.
• Sidewalk Sales: Who doesn’t love a good bargain? Old Saybrook’s sidewalk sales are the perfect opportunity to score some great deals. Local merchants set up tables and racks outside their shops, offering discounts on everything from clothing to home decor.
• Saybrook Point Boat Show: If you’re a boating enthusiast, you won’t want to miss the Saybrook Point Boat Show. Held at the Saybrook Point Marina, this event showcases the latest in boating technology and accessories. You can also check out some of the most beautiful boats in the area.
• Harbor Days Festival: This annual event celebrates Old Saybrook’s maritime history. Held in August, Harbor Days features a variety of activities, including a classic car show, a craft fair, and a parade. The highlight of the festival is the Blessing of the Fleet, where local boats are blessed for safe travels.

Music lover, bargain hunter, or boating enthusiast, Old Saybrook carries an event or festival for you. So mark your calendar and get ready to have some fun.

Accommodation Options

When you are planning a trip to Old Saybrook, you will want to make sure that you have a comfortable and relaxing place to stay. Luckily, there are a few strong accommodation options to choose from that will suit your needs and budget.

Saybrook Point Inn and Spa

If you are after a luxurious and relaxing place to stay, the Saybrook Point Inn and Spa is an excellent choice. This eco-friendly hotel sits in historic Old Saybrook along the Connecticut River. It carries indoor and outdoor saltwater pools, a full-service spa, and an on-site marina.

The guest rooms at Saybrook Point Inn and Spa are spacious and equipped with wet bars and refrigerators. You will also find bathrobes and a dressing area to make you feel like royalty. The hotel is pet-friendly, so you can bring your furry friend along for the adventure.

The full-service spa is a highlight of the hotel, running a range of treatments to help you settle and relax. You can choose from massages, facials, body treatments and more. The spa also carries a sauna, steam room and whirlpool for full relaxation.

Overall, Saybrook Point Inn and Spa suits a luxurious and pampered getaway exactly.

Golfing in Old Saybrook

You are in Old Saybrook, and you want to hit the links. Well, you are in luck because there are some strong golf courses in the area. Seasoned pro or beginner, there is a course that suits you exactly.

One of the better-known courses in Old Saybrook is the Fenwick Golf Club. This fine course sits on the Connecticut shoreline and runs long views of Long Island Sound. The course is challenging but fair, with plenty of hazards to keep you on your toes. And if you are lucky, you might even spot a celebrity out there. The club has a strict dress code, so make sure you dress appropriately before you hit the links.

Another strong option for golfers in Old Saybrook is the Old Lyme Country Club. This course sits just up the road from Old Saybrook and runs a challenging 18-hole course. The club also carries a driving range and a putting green, so you can work on your swing before you hit the course. And when you are done playing, you can relax in the club’s clubhouse and settle into a cold drink or a bite to eat.

If you are after a more low-key golfing experience, you might want to check out the Cedar Ridge Golf Course. This nine-hole course suits beginners or anyone who just wants a fun, relaxing round of golf. The course is well-maintained and runs fine views of the surrounding countryside.

No matter which course you choose, you are sure to have a strong time golfing in Old Saybrook. So grab your clubs, put on your golf shoes, and get ready to tee off.

Getting Around

You are in Old Saybrook, and you are ready to work through it. But how do you get around? Do not worry. This small town runs plenty of options to help you get from point A to point B.

First off, if you are coming by boat, you are in luck. Old Saybrook carries a marina, Saybrook Point Resort & Marina, that runs docking for transient boaters. Plus, it sits conveniently at the mouth of the Connecticut River, which makes it a strong starting point for working through the area by water.

If you are driving, there are plenty of parking options in Old Saybrook. You can park on the street, or there are several municipal parking lots throughout the town. Just be sure to check the signs for any restrictions.

If you are looking to work through beyond Old Saybrook, there are several nearby towns worth checking out. Boston and New York both sit within driving distance, and the charming towns of Old Lyme, Essex and Niantic sit just a short drive away.

And if you are after something to do within walking distance, there are plenty of options. Take a stroll down Maple Ave or Lyme St to admire the fine Georgian homes, or head to the sandcastle-filled beaches for some fun in the sun.

If you are after an unusual way to see the sights, consider taking a ride on the Essex Steam Train or a riverboat tour with the Connecticut River Museum. Both run a fun and educational way to work through the area.

In the summer, the town comes alive with community events, like the Old Saybrook Summer Concert Series, which takes place on the town green. So, driving, walking, or taking a ride on a steam train, there is plenty to see and do in Old Saybrook.

Frequently Asked Questions

What’s the best way to get around Old Saybrook without a car?

Well, you could always try hitchhiking, but we would not suggest it. Instead, why not rent a bike or take a leisurely stroll? Old Saybrook is a small town, so you will not have to worry about getting lost. Plus, you will get some exercise and fresh air. It is a win-win.

Are there any hidden gems for foodies in Old Saybrook?

Absolutely. If you are after some delicious seafood, check out Liv’s Oyster Bar. They serve some of the freshest oysters around, and their lobster roll is worth ordering. For something a little more exotic, head over to Saybrook Soup & Sandwich Co. They have got a rotating selection of soups and sandwiches that are sure to satisfy your taste buds.

Can you walk the entire length of Old Saybrook’s boardwalk without stopping?

Well, you could try, but we would not suggest it. The boardwalk is over a mile long, and there are plenty of benches and scenic spots to stop and rest. Plus, you will want to take in the long views of the Connecticut River and Long Island Sound. So, take your time and settle into the journey.

If I only have time to visit one attraction in Old Saybrook, what should it be?

That is a tough one, but we would have to go with the Katharine Hepburn Cultural Arts Center. This historic theater and museum is dedicated to the life and legacy of the legendary actress and Old Saybrook native, Katharine Hepburn. Plus, they host a variety of concerts, plays and other events throughout the year. It belongs on the list for any Hepburn fan or theater lover.

Frequently asked questions about Old Saybrook, Connecticut

Which museum in Old Saybrook is worth the time?

The Connecticut River Museum. It covers the river and the part that it played in making the whole town itself, and it runs a nature trail besides. The Florence Griswold Museum holds over 10,000 works from the Lyme Art Colony over there instead of all that. The Old Saybrook Historical Society keeps all of the town’s own artifacts and all of its own exhibits. The river one comes first, though.

Which beach in Old Saybrook can you fish from?

Town Beach. Saybrook Point works out much the same way, and both of those spots are what the locals and the visitors use for striped bass. Reel Cast Charters runs the boat option instead, half-day or full-day right out there on the water. The Sound and the river both sit right there, so the only real choice is the weather. Bring your own rod and it costs you nothing at all.

Which park in Old Saybrook has the hiking?

Rocky Neck State Park. The trails out there run through the woods and along the shoreline, and the deer and the birds are both regular out there. The Connecticut River Museum trail covers all of the marshes and the wetlands instead of that. The boardwalk is over a mile long, with the benches spaced right along the whole length of it. None of it is hard walking at all.

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