Along the coast of Connecticut, Old Saybrook is a charming destination to visit if you’re looking for a getaway on the waters of Long Island Sound. One of my favorite things about this beautiful town is it’s timeless charm, historic appeal, cultural significance, and the natural coastal beauty. Each time I visit, I fall a little bit more in love with it!
This post is all about the best things to do in Old Saybrook, CT to help you plan the perfect visit, so if you’re looking for ideas, suggestions, and tips, just keep reading 😉
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Best Things To Do In Old Saybrook, CT
1. Explore The Downtown Shops
Old Saybrook has a really cool downtown area with lots of shops, cafés, and restaurant options, so this is one area you’ll definitely want to check out on your visit.
Main Street is the best area for shopping in town, and this long stretch of road is home to dozens of stores to visit. One thing to know about this area is that it’s along the main road that runs through town, and it has multiple lanes of traffic. Because of this, it can feel a bit more busy and noisy than a quaint Main Street in a smaller town. That said, I really enjoy strolling up and down this area to browse through the shops. There’s also plenty of parking along Main Street, too, making it easy to visit.
Some of my favorite shops to visit when I’m in town are:
- Driftwood Home Decor
- Harbor Books
- Fromage Fine Foods & Coffees
- The Pursuit of Pastry if I’m in need of a sweet treat 😉
- Penny Lane Pub for a casual lunch or dinner
2. Enjoy The Summer Concert Series
Throughout the summer season, you’ll find special performances on the town green during the Summer Concert Series, which is such a fun way to enjoy the longer days during the season.
This is also a free event to enjoy, and there are various performances throughout the season, which changes every year. So, bring some blankets, a picnic, and some lawn chairs, and enjoy an evening of live music!
Pro Tip: Fromage Fine Foods is a really great place to stock up on treats and snacks to enjoy during the show 😉
3. Cruise By The Lighthouses
Old Saybrook has some beautiful lighthouses to see, but the bad news is, they’re not open or accessible to the public. The good news, however, is that you have some options to see them from the water by taking a cruise!
One of the best things to do in Old Saybrook, CT is book a cruise with Seabird. These cruises depart right from Saybrook Point Marina, making them especially convenient if you book a stay at the Saybrook Point Resort & Marina! Seabird offers a lot of different options in the area, but if you’re a lighthouse enthusiast, and that’s your main reason for heading out on the water, I recommend booking a private, custom tour, which I think is pretty affordable for the area. There are also some other wonderful choices, including a customized picnic cruise.
If the lighthouses aren’t a big deal to you, they also offer a few other options to consider, so be sure to check them all out to plan the perfect day out on the water.
4. Taste The Local Beer At Myrcene Ale Co.
Old Saybrook is home to a wonderful brewery, and if you love to try new craft brews on your travels, you’ll want to add Myrcene Ale Co. to your itinerary. Specializing in IPA’s, Myrcene aims to keep the craft brew scene simple and approachable, and the down-to-earth vibe here is really great.
If you’re not into beer, they also offer canned cocktails and hard cider, so everyone in your group will find something to sip on 😉
5. Relax At Harvey’s Beach
Old Saybrook doesn’t have a strong beach presence, but if you’re looking to get your feet in the sand, and toes in the water, then you’ll want to head over to Harvey’s Beach. This small but lovely beach has soft, sandy shoreline to explore, and also offers really nice sunsets. In fact, it’s one of the best areas in town to watch a sunset!
But I always like to recommend you set expectations when visiting: Harvey’s Beach isn’t a sprawling destination, and is more of a quaint area in town to enjoy the water, so keep that in mind. It’s really nice to see when visiting, though, and I highly recommend coming for sunset, even if you’re not looking to go for a swim.
6. Enjoy The Views From The Causeway
One of my personal favorite things to do in Old Saybrook, CT is take a walk on the Causeway, which connects the marina with Fenwick, a borough in the town. I love taking in the views of the water here, and I’m so happy that it has a walking path just for pedestrians, so you’re not sharing the road with cars.
From the causeway, you’ll get a distant view of Lynde Point Lighthouse and the Connecticut River, and it’s a nice, easy stroll to take to admire the waterfront scenery.
7. Experience The Katharine Hepburn Cultural Arts Center
Fun fact: Old Saybrook was the summer home of famous actress Katharine Hepburn! It’s also where she lived in her later years, and the house she owned still stands in Fenwick. Katharine Hepburn Cultural Arts Center was named in her honor, and it’s home to both the Katharine Hepburn Museum, as well as a performing arts venue.
The museum is where you can see real memorabilia from Katharine’s life, including some of her own clothing, costumes from movies, home movies, some of her awards, and lots more. If you’re a fan of old Hollywood, this is really such a cool spot to check out when you visit.
Also, the live music venue inside The Kate, as the locals call it, aims to provide the town with exciting performances and events throughout the year. During your visit, it’s worth checking out the schedule to see what’s going on, and get some tickets for a show! There’s always such a great mix of events that range from concerts, movies, comedy, musicals, and even events geared toward children.
8. Have A Wonderful Meal At Liv’s
One of the most popular restaurants in Old Saybrook is Liv’s, and for very good reason! There are two options when dining here: their oyster bar restaurant on Main Street, and their seafood shack at the marina. They both have completely different vibes, as the oyster bar is a traditional restaurant that feels both cozy and upscale, and Liv’s Shack at the marina is a very casual seafood joint.
Both specialize in awesome, fresh seafood, though, so you’ll get that regardless of where you choose to go.
Liv’s Shack has excellent lobster rolls, fish tacos, and more casual fare like hot dogs and burgers. You’ll want to head to the oyster bar for, well, oysters, of course! They also have a full raw bar, and a variety of entrees to choose from.
9. Grab Some Ice Cream At Fenwick’s
If you’re looking for a sweet treat after dinner, head to Fenwick’s! This is my favorite ice cream in town, and for over 30 years, they’ve been serving up their homemade ice cream to locals and visitors. It’s even been voted as the best ice cream in Connecticut four times!
The little unassuming shack is pretty small, and lines can get long on summer weekends, but it’s worth the wait. They specialize in their homemade hard ice cream, but also offer flurrys and sundaes, and they always have a variety of flavors to choose from.
10. Enjoy The Scenery At Fort Saybrook Monument Park
A short walk from the Marina is Fort Saybrook Monument Park, and while this area is small, it offers some fun things to do, and lovely coastal views.
There’s a really nice little boardwalk and viewing area overlooking the salt marshes, which is especially perfect for spotting wildlife and birds. Nearby the boardwalk, history buffs will want to keep an eye out for the signs that showcase the story of the town’s history.
A bit further from the boardwalk, you’ll stumble upon a waterfront area that has a mini golf course, a pavilion, and a waterfront walkway with benches that overlook the harbor.
Things To Do In Old Saybrook In The Winter
11. Experience The Torchlight Parade
One of the best things to do in Old Saybrook in the winter is experience the Torchlight Parade, which is typically held the second Saturday in December as a fun way to celebrate the holiday season. This parade features costumed Fife and Drum Corps from all over New England, parade floats, and ends with Santa’s arrival as the grand finale.
12. Skate On Exchange Pond & Build A Snowman!
When the weather is cold enough in the winter, the parks and recreation department in Old Saybrook offers ice skating on Exchange Pond. And they’ll do all the work for you to ensure the ice is safe for skating! On weekends, they’ll also have a warming fire pit going, and some special skating events with lights.
Each year, the parks department also hosts a Snowman Building Championship, typically held in February. This event is for the kids, and takes place on the town green. If you’re visiting in the winter, it’s really cute to walk around afterwards and enjoy all the adorable snowmen.
13. Book A Restorative Spa Day
Winter is always the perfect time for self care, and one of the best things to do in Old Saybrook in the winter is enjoy some pampering with a spa day.
There are three really great places in Old Saybrook for massage and pampering: Bliss Spa, the Spa at Saybrook Point, and the Spring Wellness Center. Each of these offers different options for massage, as well as other services like cupping, reflexology, facials, and more.
Where To Stay In Old Saybrook, CT
Oddly enough, there aren’t a lot of nice hotels right in Old Saybrook, but here are my top suggestions on where to stay when visiting the area:
Saybrook Point Resort & Marina: This is the absolute best place to stay in town on your visit. This waterfront resort has a restaurant that’s right on the harbor, and offers really wonderful coastal views. If you’re looking to plan a relaxing getaway, this is 100% where I recommend you stay.
Westbrook Inn Bed & Breakfast: Located just a few minutes outside of Old Saybrook, this is the next best option. This cozy, New England style inn is also right on the river, and there’s a lot of outdoor space to enjoy at the inn. They also offer complimentary breakfast with your stay, and smart TV’s in the rooms for streaming your favorite shows and movies.
Things To Do Near Old Saybrook, CT
While staying in Old Saybrook, there are also so many wonderfully fun things to check out nearby, so I wanted to be sure to give you the inside scoop on what’s worth doing that’s just a short drive away 😉
14. Explore The Nearby Beaches
Within 30 minutes of Old Saybrook, you’ll find some really wonderful beaches to spend that day at, and my favorites to suggest are: Rocky Neck State Park Bathing Beach, Ocean Beach Park, and Hammonasset Beach State Park.
Rock Neck State Park in Old Lyme is about 20 minutes from Old Saybrook, and a really nice beach to check out during your visit. The shoreline is very sandy, and there’s a nice pavilion, changing rooms, bathrooms, etc. There is a fee to enter, but the beach is open to the public, and there’s lots of parking.
Ocean Beach Park in New London is about 30 minutes from Old Saybrook, and this is a really good choice is you’re traveling with kids. While the beach is really nice for swimming with a sandy shoreline, there’s also a small amusement park with rides, arcade games, and on-site dining, making this an entire destination for a beach day. This beach is open to the public, and charges a fee to get in, but there’s tons of parking available.
Hammonasset Beach State Park in Madison is about 20 minutes from Old Saybrook, and is home to a very large, 2-mile long sandy beach. This option is great for anyone looking to spend the whole day here because there’s also nature and walking trails, trails for riding your bike, and observation areas to admire the scenery. I really love this one! This beach is open to the public as well, and there’s a fee to enter, but there’s plenty of parking.
15. Take A Day Trip To Block Island
If you’re looking for a really fun day trip option during your stay in Old Saybrook, I really love to suggest taking the ferry over to Block Island. It’ll make for a longer day, but Block Island is pretty small, and it’s easy to see a lot in just a day. It also offers unique scenery that’ll differ from Old Saybrook, and has beautiful beaches, a cute little downtown for shopping, nature and hiking trails, and the ride over on the ferry is short and fun!
Psst! I have an entire post all about taking a day trip to Block Island, if you’re looking for more info 😉
16. Spend The Afternoon In Essex
Only 10 minutes from Old Saybrook is the darling little town of Essex, which is one of my favorite small towns in Connecticut! Essex offers some of the most idyllic New England charm, and makes for a very easy, laid back afternoon trip from Old Saybrook because it’s very small.
There’s a small Main Street in Essex with cute little shops to visit, the very cool Essex Steam Train & Riverboat tours, great places to eat, a wonderful little ice cream place, and even a nice park off main Street that’s perfect for packing a picnic.
Psst! I have an entire post all about things to do in Essex, CT, if you’re looking for more ideas 😉
17. Explore Quaint Chester
Another wonderful little gem that’s just just about 5 minutes past Essex, and only about 15 minutes from Old Saybrook, is Chester. This is another one of my favorite small towns to explore in the area, and you can easily see both Essex and Chester in the same afternoon.
Chester is home to a great little brewery, an adorable Main Street with unique shops, an awesome ice cream place, and beautiful scenery.
Psst! I also have an entire guide on things to do in Chester, CT, if you’d like more ideas and photos 😉
18. Explore Westerly, Rhode Island
About 35-40 minutes from Old Saybrook is Westerly in Rhode Island, which is also home to the cute little village of Watch Hill. I really love to suggest this area for a day trip, too, as there’s a great mix of coastal scenery, beaches, and two great little downtowns to enjoy.
Watch Hill is so charming, and I highly recommend stopping by if you visit Westerly. The downside to be aware of is that parking here is very limited, and also only allows you to park in 2-hour increments. But the good thing is, if you don’t stay and linger at the beach in Watch Hill, you can easily stroll through town and see the highlights in 2 hours. This includes the Main Street for shopping, views from Napatree Point, Watch Hill Lighthouse, and the famous Ocean House resort (which is worth the walk over just to see it!).
While in Westerly, you can spend the day at Misquamicut State Beach, which is open to the public, enjoy Westerly’s downtown with nice shops and restaurants, and sip on local brews at the very cool Grey Sail Brewing.
Psst! You guessed it! I also have an entire guide on things to do in Westerly, RI and Watch Hill if you’d like more ideas 😉
19. Visit Gillette Castle State Park
About 30 minutes from Old Saybrook is the very cool Gillette Castle State Park, which will make you feel as though you’ve been transported to Europe. This historic, medieval castle was built in 1919 on a hill overlooking the Connecticut River, and now, both the grounds and the castle are open to the public.
There’s a small charge to tour the inside of the castle, but the grounds and surrounding park are open year-round and are free to visit. It’s worth it to tour the castle, though, if only for the view of the river, and to get the full experience while you’re there.
20. Tour The Local Wineries & Vineyards
Did you know that there are over 50 wineries in Connecticut? And they’re actually pretty well scattered all over the state, so it’s pretty easy to visit at least a couple whenever you decide to stay. And there are some nice options close to Old Saybrook!
The two wineries closest to Old Saybrook are Chamard Vineyards, and Bishop’s Orchards Winery. If you’re willing to drive a bit further, Paradise Hills Vineyard & Winery and Gouveia Vineyards are both about 45 minutes away and worth visiting.
If you happen to take a day trip over to Mystic (which is my next suggestion!), you’ll find a few more wineries nearby, including one of my favorites, Stonington Vineyards. But some more really nice ones are near this area, too, including Preston Ridge Vineyard, and Saltwater Farm Vineyard.
21. Spend The Day In Mystic
Last but definitely not least, Mystic is only about 30 minutes from Old Saybrook, and very much worth visiting on your trip! This small little town along Mystic River offers so much to do, including the wineries mentioned above, a wonderful Main Street with shops and restaurants, the amazing Mystic Seaport Museum, and the very unique and cool Olde Mystik Village shops (which was used as the set for the Hallmark movie Mystic Christmas).
Psst! Yep, I have a guide all about the best things to do in Mystic, CT, too, if you want to check that out!
Things To Do In Old Saybrook FAQ
Best Time To Visit Old Saybrook
Old Saybrook tends to be pretty seasonal, with the summer being the best and busiest time to visit. June-September is when you’ll experience the most crowds, but the best weather, making this an ideal time to visit. And while summer is the busiest and most lively season in Old Saybrook, I’ve never found it to be overly crowded, and it still felt rather peaceful.
However, because Old Saybrook doesn’t have a big beach scene, it honestly makes for a wonderful getaway year-round. While some businesses and such are only open seasonally, much of the town is open all year. Spring and fall are especially great if you’re looking for a shoulder season visit.
If you happen to visit in July and August, you’ll also get to see the hydrangeas in full bloom, which is always a treat!
Is Old Saybrook Walkable?
Yes and no. As mentioned, the main downtown area is filled with shops and restaurants along the main road, and while it’s walkable, it is a main road with multiple lanes of traffic. So, the noise from the road makes it slightly less than ideal. That said, this area of Old Saybrook is very walkable.
To get around to some other restaurants and the waterfront, though, you’ll need to drive, so having a car is necessary.
Is Old Saybrook Worth Visiting?
If you’re already visiting Connecticut’s coastline, Old Saybrook is absolutely work visiting! What is lacks in great beaches, it makes up for in beautiful coastal scenery, shopping, cultural activities, and a really nice waterfront resort.
Of all the destinations to visit in New England, however, I wouldn’t necessarily say it’s worth going out of your way for. As much as I love to explore Connecticut, for first time visitors in New England, it is rather far from many of the top attractions. However, if you’ve been to this area before, and are looking to explore a place you’ve never been, I really love to suggest Old Saybrook!
Is Old Saybrook Good For A Beach Vacation?
I wouldn’t recommend Old Saybrook if you’re exclusively looking for a beach getaway. There aren’t a lot of public beaches right in Old Saybrook, and the best one, Harveys Beach, is not very big. If you’re looking for a beach vacation in this area, I’d recommend Madison, Westport, or Westerly, RI over Old Saybrook.
That said, if you don’t mind driving to some nicer, bigger beaches, Old Saybrook makes for a nice home base! As mentioned, there are three fantastic public beaches that are 30 minutes or less from town.
More posts you may enjoy:
- Summer In Connecticut: Where To Go & What To Do!
- The Ultimate Summer In New England Guide
- Things To Do In Niantic, CT
- Best Beach Towns In New England
- Best New England Day Trips
- Where To Find The Real Stars Hollow From Gilmore Girls
That’s A Wrap On Things To Do OId Saybrook, CT
And there you have it, all the very best things to do in Old Saybrook, CT to add to your itinerary. Whether you’re looking for a romantic day trip to explore the shops and waterfront, or you’re planning a getaway at the Saybrook Point Resort to explore even more, chances are, you’ll have a perfectly relaxing trip. Happy planning!
