Old Saybrook is one of the oldest towns in Connecticut, conveniently located halfway between Boston and New York to provide easy weekend access to its charming Main Street full of unique shops, restaurants, and galleries.

There is always something going on in the summer: An arts and craft show, boat shows, the Taste-of-Saybrook Fest, sidewalk sales, the Summer Pops Concert, and weekly outdoor concerts on the town green. Don’t miss a production at Kathryn Hepburn Theater or an art exhibition at the Artisan Harbor. Take a stroll to the historic Lynde Point Lighthouse on Long Island Sound and visit the beautiful Georgian Gen. William Hart House, built in 1767.

1. The Katharine Hepburn Cultural Arts Center

The Katharine Hepburn Cultural Arts Center
© The Katharine Hepburn Cultural Arts Center

Located in the historic 1911 former town hall on Main Street in Old Saybrook, Connecticut, the Katharine Hepburn Cultural Arts Center, or the Kate as it is known locally, is a non-for-profit performing arts organization that offers a lasting legacy to the iconic actress Katherine Hepburn. The center also provides opportunities in arts education and offers a range of performing arts productions in their charming 250-seat theater, in music, opera, comedy, dance, film, and children’s programming. There is a small museum in the theater lobby honoring the legendary actress Katherine Hepburn, the city’s most celebrated resident. Every year, the center puts on about 216 performances, serving almost 40,000 theater lovers. More things to do in Connecticut

300 Main St, Old Saybrook, CT 06475

2. General William Hart House

General William Hart House
© General William Hart House

The Gen. William Hart House is a historic house built in 1767 in Old Saybrook, Connecticut. The house was built for General William Hart at the time of his marriage. He was a noted politician of the time and colonial militia leader. The house is on the National Register of Historic Places and is part of the Old Saybrook South Green historic district. A great example of Georgian residential architecture, the Hart House is a two and a half story wood frame structure with a gabled roof and five bays, clapboard exterior, and two chimneys. Its central entry is sheltered by a gable-roofed portico with two Doric columns. Many of the interior features have been preserved, including the ornate fireplace surrounds. The house and the surrounding gardens are owned by the Old Saybrook Historical Society

350 Main St, Old Saybrook, CT 06475

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3. Lynde Point Lighthouse

Lynde Point Lighthouse
© FLX2/stock.adobe.com

The Lynde Point Lighthouse is located on the Long Island Sound in Old Saybrook, Connecticut, on the mouth of the Connecticut River. The original light was a 35-foot-tall wooden tower completed in 1803. When a new lighthouse was needed, it was designed as 65-foot octagonal brownstone tower. It was built in 1838 and lit for the first time in 1839. The new lighthouse was renovated in 1867 and the keeper's house was replaced in 1858 with a gambrel-roofed wooden house in Gothic revival style. The house was torn down in 1966 and replaced by a duplex. In 1852 the original lamps were replaced first with a fourth-order Fresnel lens and in 1890 with a fifth-order Fresnel lens. Lynde Point Lighthouse was fully automated in 1978. It is listed on the National Register of Historic Places.

102B Sequassen Ave, Old Saybrook, CT 06475-3116

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4. Fenwick Golf Club

Fenwick Golf Club
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Your next great golfing adventure awaits at 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 golfers with alluring views of the Long Island Sound, the South Cove, and the river as they progress through the 9 holes.

580 Maple Ave, Old Saybrook, Connecticut 06475, Phone: 860-388-2516

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5. Reel Cast Charters

Reel Cast Charters
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If you are interested in the best inshore angling experience in the Northeast, you need Reel Cast Charters from Old Saybrook, Connecticut. 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. Their clients 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.

Old Saybrook, CT 06475, Phone: 203-710-5116

6. Florence Griswold Museum

Florence Griswold Museum
© Florence Griswold Museum

The Florence Griswold House in Old Lyme, Connecticut, used to be a boarding house owned by Florence Griswold. After the artist Henry Ward Ranger stayed at the house, he invited his other artists friends and soon a large number of American Impressionist artists moved to Miss Florence’s boarding house, forming the Old Lyme Art Colony, the heart of development of American Impressionism. The building now houses the Florence Griswold Museum and is registered as a National Historic Landmark. The museum’s collections include some of the most prominent American artists of the late 19th and early 20th centuries, many of whom painted on the walls and doors of Miss Florence Griswold’s boarding house. The museum is furnished with a number of fine and decorative artifacts from the collections. In 2001, the museum acquired the collection of the Hartford Steam Boiler Inspection and Insurance Company, adding 157 oil paintings, 31 works on paper, and 2 works of sculpture, all Connecticut-themed, to the permanent holdings. The museum's 9,500-square-foot Robert and Nancy Krieble Gallery was opened in 2002.

96 Lyme St, Old Lyme, CT 06371

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7. Fresh Salt

Fresh Salt
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Voted Best Sunday Brunch in 2016 by the Connecticut Magazine, Fresh Salt is an elegant upscale restaurant with subtle New England coastal decor, a cozy club vibe, spectacular views of the Connecticut River from every seat in the house, and superb fresh American seafood. They serve lunch, dinner, and cocktails and you can choose between the elegant dining room, the relaxed Fresh Salt Lounge, and the lively outdoor Marina Bar. Fresh Salt works with local farmers, fishermen, and artisans to provide fresh ingredients for their locally inspired seasonal menus. Chef de Cuisine, Lou-Anne Langlois, a Connecticut native, offers a range of New England coastal dishes prepared with her own flair. Try her coconut-scallion crusted Atlantic cod with lemongrass jasmine rice, toasted cashews, carrots and curry cream.

2 Bridge St, Old Saybrook, CT 06475, Phone: 860-388-1111

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8. Penny Lane Pub & Restaurant

Penny Lane Pub & Restaurant
© Penny Lane Pub & Restaurant

Penny Lane Pub is a charming English-style pub and restaurant located in a two-story building in historic Old Saybrook, Connecticut. 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.

150 Main St, Old Saybrook, CT 06475, Phone: 860-388-9646

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9. Aspen Restaurant

Aspen Restaurant
© Aspen Restaurant

Aspen Restaurant in Old Saybrook, Connecticut, is a sophisticated space with classic elegance, a cozy fireplace, a gleaming mahogany bar with a large granite top, and a pleasant and comfortable club atmosphere. Beautiful alabaster sconces with wrought iron detail and arched floor-to-ceiling windows provide plenty of light. Aspen offers contemporary American cuisine prepared from seasonal, highest quality, sustainable ingredients. Executive Chef Tom Prue offers a New American seasonal menu with a wonderful selection of small plates perfect for sharing. For main course, try his delicious rabbit cassoulet with confit rabbit leg, chicken sausage, pork belly, and cassoulet beans. The wine list is not large but is well-selected and it offers wines from all over the world and for every budget.

2 Main St, Old Saybrook, CT 06475, Phone: 860-395-5888

10. Things to Do Near Me: Monkey Farm

Things to Do Near Me: Monkey Farm
© Monkey Farm

Located in the historic 1800 Old Stage Inn in Old Saybrook, Connecticut, Monkey Inn is a popular local hangout and watering hole that also offers great food. Exposed beams of the old inn and plenty of dartboards on the walls create a relaxed barroom atmosphere where you can bring the family for a Sunday meal or hang out with friends watching the game on the TV or playing pool. When the weather permits, the wonderful wraparound porch is the place to be. The menu ranges from classic pub grub such as burgers, sandwiches, and pizza to delights such as scallops casino roasted with garlic, bacon, and peppers. The owners says that the only monkeys you will find in the inn are sitting next to you at the bar.

571 Boston Post Rd, Old Saybrook, CT 06475, Phone: 860-388-4866

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11. Liv's Oyster Bar & Restaurant

Liv's Oyster Bar & Restaurant
© Liv's Oyster Bar & Restaurant

Opened in 2006, Liv’s Oyster Bar and Restaurant is an upscale, very elegant place where John Brescio, the owner and Liv’s Executive Chef, creates simple, seafood-focused dishes using fresh local ingredients and the bounty of seafood from the local area. The menu changes with seasons, bringing guests a true taste of the Connecticut coast of Long Island Sound. Whether you dine in the main room, at the bar, or on the patio, it is an experience to be shared with friends and family. The guests are greeted at the entrance with a magnificent mural of a coastal scene, and the brick-walled dining room is sparkling with bright white tablecloths, mirrors, and chandeliers. The fully stocked bar is on the one side and the loaded raw bar is on the other, competing for the attention.

166 Main St, Old Saybrook, CT 06475, Phone: 860-395-5577

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