Things to Do in Old Saybrook

By VI | Disclosure: I use affiliate links

Alex Krassel/stock.adobe.com

If you’re looking for coastal charm with historic roots, I always say—head to Old Saybrook. I’ve spent many peaceful afternoons here, where the Connecticut River meets Long Island Sound. You’ll love how it blends maritime history, boutique shopping, and beachside calm. Whether I’m wandering down Main Street or catching the sunset at Harvey’s Beach, I always find that classic New England charm. You’ll feel it the moment you arrive.

Old Saybrook, CT Highlights:

Explore Main Street: I could spend hours browsing local shops and art galleries—you’ll enjoy the cozy cafés and small-town feel just as much as I do.
Relax at Harvey’s Beach: I’ve brought a book, a blanket, and just let the waves do the rest. You’ll love the calm waters and sunset views—it’s perfect for families or just some solo peace.
Visit the Katharine Hepburn Cultural Arts Center ("The Kate"): I’ve caught some wonderful performances here, and you can enjoy the charm of a historic theater named after Old Saybrook’s beloved star.
Stroll Saybrook Point: I always make time to walk the waterfront, soak in the lighthouse views, and treat myself to a nice dockside meal. You’ll find it peaceful and picturesque.
Discover Fort Saybrook Monument Park: I’ve learned quite a bit here—interpretive signs and scenic walkways make this a great spot if you’re curious about the town’s colonial past. You’ll walk away with a deeper appreciation.

Best Time to Visit Old Saybrook, CT

In my experience, the best time to visit is from late spring through early fall (May to October). You’ll enjoy warm beach days, lively outdoor events, and crisp fall foliage as the crowds thin out. I’ve visited in every season, but I always aim for those golden-weather months when the town truly shines—and I think you’ll agree.

How to Get to Old Saybrook, CT

If you are traveling by car: I’ve driven in from both New York and Boston—it’s an easy ride on I-95. You’ll get here in about 2.5 hours from NYC or 2 hours from Boston, depending on traffic.
By train: I love that you can take Amtrak or Shore Line East right to Old Saybrook station. It’s convenient and connects you to other great coastal towns too.
By bus: I’ve used regional bus services before—they’re reliable and connect you with nearby cities like Hartford and New Haven. You’ll have options whether you’re planning a car-free getaway or not.

Where to Stay in Old Saybrook, CT

Saybrook Point Resort & Marina – When I’m after a little luxury, this is where I stay. You’ll love the marina views, relaxing spa, and pools that make it easy to unwind.
Liberty Inn – I’ve stayed here when I wanted something simple and budget-friendly. You’ll appreciate the location—close to downtown and just off Route 1.
Bee and Thistle Inn (nearby in Old Lyme) – If you’re in the mood for romance and a bit of history, I recommend this charming B&B just minutes away. I’ve always felt like I stepped back in time.