Looking for coastal charm with historic roots? Discover Old Saybrook! Nestled where the Connecticut River meets Long Island Sound, Old Saybrook blends maritime history, boutique shopping, and beachside beauty. Whether you're strolling Main Street or soaking in the sun at Harvey’s Beach, this shoreline town delivers classic New England vibes year-round.
Old Saybrook, CT Highlights:
- Explore Main Street: Wander through unique shops, art galleries, and cozy cafés in a quaint downtown district.
- Relax at Harvey’s Beach: Enjoy soft sands, calm waters, and sunset views at this family-friendly beach.
- Visit the Katharine Hepburn Cultural Arts Center ("The Kate"): Catch live performances in a historic theater named after Old Saybrook’s most famous resident.
- Stroll Saybrook Point: Take in scenic harbor views, lighthouse vibes, and waterfront dining.
- Discover Fort Saybrook Monument Park: Learn about the town’s colonial origins with interpretive signs and scenic walkways.
Best Time to Visit Old Saybrook, CT
The best time to visit Old Saybrook is from late spring through early fall (May to October). Summer brings beach weather and vibrant outdoor events, while fall offers colorful foliage and coastal crispness without the crowds.
How to Get to Old Saybrook, CT
- If you are traveling by car: Easily accessed via I-95, Old Saybrook is about 2.5 hours from NYC and 2 hours from Boston.
- By train: Amtrak and Shore Line East trains serve the Old Saybrook station, connecting the town to major cities and coastal communities.
- By bus: Regional bus services connect Old Saybrook with Hartford, New Haven, and other towns across Connecticut.
Where to Stay in Old Saybrook, CT
- Saybrook Point Resort & Marina – Waterfront luxury with a spa, indoor/outdoor pools, and serene marina views.
- Liberty Inn – Simple, budget-friendly option located just off Route 1 and close to downtown.
- Bee and Thistle Inn (nearby in Old Lyme) – Romantic bed & breakfast in a historic 18th-century home just minutes away.
Best Things to Do in Old Saybrook, CT
1. Stop by The Kate to see the museum dedicated to Katherine Hepburn
Rating: ★★★★★
I took a 40-minute CTrail Shore Line East train from New Haven to Old Saybrook on a quick coastal day trip.
I started my visit at the small museum at the Kate (short for the Katharine Hepburn Cultural Arts Center). My walk from the train station was about 15 minutes.
The museum is right in the lobby and lets you learn about the legendary actress Katherine Hepburn, the city’s most celebrated resident.
If you are staying overnight, you can come back in the evening and see a show.
Address: 300 Main St, Old Saybrook, CT 06475
2. Step inside the General William Hart House
Next I visited the General William Hart House which dates back to 1767.
The house was built for General William Hart at the time of his marriage.
The house is on the National Register of Historic Places and is part of the Old Saybrook South Green historic district.
I loved the gardens which were included in the $5 admission fee.
Many of the interior features have been preserved, including the ornate fireplace.
Address: 350 Main St, Old Saybrook, CT 06475
If you are a photographer, don't miss:
3. Take a photo at the Lynde Point Lighthouse
I caught up with some friends in Old Saybrook and we drove out to the Lynde Point Lighthouse, located on the Long Island Sound in Old Saybrook, Connecticut, on the mouth of the Connecticut River. The drive from downtown took about 10 minutes.
There is a nice semi-circular viewing area that makes you feel like you are levitating above water.
I enjoyed learning about the history of the lighthouse. The original light was a 35-foot-tall wooden tower completed in 1803.
Address: 102B Sequassen Ave, Old Saybrook, CT 06475-3116
Activities and Attractions for Couples:
4. Practice your swing at Fenwick Golf Club
One of my friends is a golf fan, so he insisted on driving us to Old Saybrook’s Fenwick Golf Club. Fenwick is beloved for being Connecticut’s oldest public golf course. When it comes to golf courses in general, Fenwick is the second oldest course in the state (following the Greenwich Golf Club), with its first three holes being established in 1894.
Fenwick’s 9-hole course was completely finished in 1896 and has since then been challenging golfers with its unique link design, natural greens, difficult topography, and the challenging breeze that requires precise golfing. The course is perched at the mouth of the Connecticut River and provides you with alluring views of the Long Island Sound, the South Cove, and the river as they progress through the 9 holes.
Address: 580 Maple Ave, Old Saybrook, Connecticut 06475, Phone: 860-388-2516
Stay at Saybrook Point Resort & Marina if you want a luxury room with a view.
5. Go fishing with Reel Cast Charters
I heard great things about Reel Cast Charters for people who like to go fishing. It is an experienced fishing guide service that has carved a niche in sportfishing in the Northeast by providing an unique experience to passionate anglers – going for trophy-sized striped bass with light tackle.
There is no oversized conventional reel and no trolling. You fish with live baits and artificial lures for big fish.
They specialize in the Connecticut side of Long Island Sound. While they encourage catch and release fishing, which benefits the future of the sport of fishing, they are happy to fillet your catch if you wish to keep it for dinner. Their boat is on a trailer, so they can quickly get to a hot bite location.
Address: Old Saybrook, CT 06475, Phone: 203-710-5116
6. Have lunch or dinner at Penny Lane Pub & Restaurant
For lunch cheack out Penny Lane Pub & Restaurant a charming English-style pub and restaurant located in a two-story building in historic Old Saybrook.
Spacious and bright, both the indoor and outdoor spaces have a friendly neighborhood atmosphere, perfect for hanging out with friends or bringing the family for some comfort food.
Besides a variety of quality, upgraded pub fare, they also have creative daily specials, affordable prix fixe dinners, and a great selection of craft beers and specialty wines.
Try their half-pound Angus burgers, shepherd’s pie, steaks, and fish and chips.
If you are coming for dinner, check their delicious Cabernet-braised short ribs with a vegetable ragout, green beans, and mashed potatoes.
The best time to go is on Saturday and Sunday, when there is live entertainment in downstairs pub.
Address: 150 Main St, Old Saybrook, CT 06475, Phone: 860-388-9646
If you have time to explore another small town in this area, head to East Lyme where I enjoyed a stroll on the boardwalk.
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