Old Saybrook, CT

Spring has bloomed in Connecticut for the last couple weeks along with warmer temperatures! One Sunday was a beautiful day for walking around outdoors so my husband, our ‘doghter’ and I headed up to Old Saybrook, CT. We have only driven through the town but never explored the area. Only a quick 40 minutes on I-95 from Mystic, we were surprised that it took us so long to visit! Old Saybrook is a beautiful coastal town located on Connecticut River.  

Whatever it is, the way you tell your story online can make all the difference.

Old Saybrook Chamber of Commerce.

Once we were in the town, we drove around a bit for some sight seeing and no plans of where to go. We stopped at the Smithland Supply store first, a pet and garden center. An impressive store for your garden and pet needs! Our doghter beelined to the section overflowing with her favorite treats from Earth Animal (based in Westport, CT). The staff were super friendly and very helpful.

Smithland Pet & Garden Center.

Smithland Pet & Garden Center.

Earth Animal galore!

Earth Animal galore!

We headed to the Fenwick section of Old Saybrook, to see the two lighthouses. Lynde Point and Saybrook Breakwater. Both are not accessible by cars, but we were able to see it from a distance. The Lynde Point is right next to a beautiful golf course! 

View of water in Fenwick section of Old Saybrook.

View of water in Fenwick section of Old Saybrook.

From there, we drove over to Saybrook Point. A waterfront area with beautiful views of the Long Island Sound. Also where Fort Saybrook Monument Park is located. The park has 17 acres with a scenic route next to the Sound. The Fort was built in 1636, there was a statue dedicated to the builder of the Fort. There also were old railroad train tracks and wheels as it was a former site of the Connecticut Valley Railroad’s roundhouse. As you walk around, you will see several markers with historical information about the fort. 

Fort Saybrook with my pup.

Fort Saybrook with my pup.

Railroad history at Fort Saybrook.

Railroad history at Fort Saybrook.

Love those stone walls in Fort Saybrook.

Love those stone walls in Fort Saybrook.

Right next to the Fort, is the Saybrook Point Resort and Marina. A luxury resort that perches right on the Sound. The resort has always come highly recommended as long I have lived in Southeastern CT, but I personally have never stayed there. The resort also has dining, I’ve heard many ravings about the brunch at Fresh Salt. Someday, I will have to stay there! We walked around on the grounds, there was a marina there too. The path was lined with wood carved poles of nautical animals such as lobster, crab, octopus, seal, etc. It was the coolest thing! There were so many walkable sidewalks around the resort where you could enjoy the waterfront views and beautiful homes that lined the street. 

Wood carved lobster pole by the marina.

Wood carved lobster pole by the marina.

Wood carved swordfish pole.

Wood carved swordfish pole.

How cute is this one?! Wood carved seal.

How cute is this one?! Wood carved seal.

Saybrook Point Resort had this fun selfie station.

Saybrook Point Resort had this fun selfie station.

Colorful bikes outside of Saybrook Point Resort.

Colorful bikes outside of Saybrook Point Resort.

Another cool wood carved sculpture near the resort.

Another cool wood carved sculpture near the resort.

A gorgeous guest inn on the street near the resort.

A gorgeous guest inn on the street near the resort.

Another gorgeous guest inn.

Another gorgeous guest inn.

Beautiful spot to walk around in Saybrook Point.

Beautiful spot to walk around in Saybrook Point.

Old Saybrook definitely had no shortage of beautiful homes, some were historical too. We headed over to Main Street where there are several shops and restaurants. Before we checked out them, we walked down the sidewalk into the residential area to enjoy the beautiful homes. We also saw some historical buildings such as churches, a pharmacy and museums. There are definitely plenty of walkable paths all over Old Saybrook. It’s perfect for days when you just want a long walk to enjoy the beautiful weather. 

Historical site on Main Street - first used as a general store then a pharmacy. It was a bed and breakfast until it closed in 2019.

Historical site on Main Street - first used as a general store then a pharmacy. It was a bed and breakfast until it closed in 2019.

One of many beautiful homes on Main Street.

One of many beautiful homes on Main Street.

Loved the flag and the flower boxes.

Loved the flag and the flower boxes.

One of the historical buildings on main street was the former Town Hall which currently houses ‘The Kate’, Katharine Hepburn Cultural Arts Center. It is a theater that has performances including theater, music, films, etc. There is also a museum dedicated to Katharine Hepburn’s acting career. Unfortunately while I was there, it was being renovated. Why is it named after Katharine Hepburn, known as a Hollywood actress? She has ties to Old Saybrook, dating back to 1912 when her family owned a summer house. Hepburn returned to Old Saybrook often before she retired to her home in Fenwick section (near the Lynde Point Lighthouse) in 1997. She lived her remaining years there until she passed away in 2003. 

Passed by this cute library!

Passed by this cute library!

On the main street, there were several shops. Of course, our favorite kind to check out is antiques. It’s fun to poke around antiques shops! My favorite women’s clothing store in Old Saybrook is ‘Pearls and Plaid’ which sells so many cute coastal themed goods! They expanded with their new store for men called Post Road Supply which is right next door. 

Blooms everywhere in Old Saybrook!

Blooms everywhere in Old Saybrook!

Where to eat in Old Saybrook? No worries, I wouldn’t let you go without some suggestions! As you may or may not know, I follow a gluten and dairy free diet. A while ago, I discovered Shayna B’s by the Sea, a dedicated gluten free and vegan cafe located right on the main street. On this Sunday, I was determined to stop there to get my favorite cookie dough truffles. They offer sweets such as brownies, cupcakes, cookies and other pastries such as pop tarts and bagels. The cafe also serves sandwiches, soups, pizzas, burgers and more. For those who aren’t on a gluten free diet, Mystic Market has a location in Old Saybrook which has amazing sandwiches to go. If you’re in the mood for seafood, Skipper’s Seafood is the classic stand offering sandwiches, soups, salads, etc. Pasta Vita is also a good option for grabbing gourmets meals to go! There are plenty of restaurants options in Old Saybrook! 

UPDATE: Shayna B’s by the Sea relocated to Westbrook, CT.

Shayna B’s by the Sea.

Shayna B’s by the Sea.

I couldn’t wait to taste them before taking this photo!

I couldn’t wait to taste them before taking this photo!

The fire dog had to swing by the house!

The fire dog had to swing by the house!

It’s easy to make a day out of it in Old Saybrook with plenty walkable routes with scenic views, visit the small museums to learn about the town’s history, enjoy eating at one (or a few) of many restaurants, stop by Harvey’s Beach, see the lighthouses, play some golf and so on! If you want to make a weekend out of it, which will be easy to do with so much to see, Essex is right next door. I wrote about Essex recommendations here and here. We had a fun day exploring the beautiful town of Old Saybrook and we definitely will be back! 

I love shoreline businesses logos like this!

I love shoreline businesses logos like this!