For some, Connecticut is merely a stop on the way to “real New England.” But for those who linger long enough, the Nutmeg State reveals its authentic charm. From scenic coastlines and maritime history to spectacular food and vibrant small towns, Connecticut offers a mix of attractions that appeal to every type of traveler. Lonely Planet inspired with their top 18, so here is our “local guide” version.
With its blend of natural beauty, historical significance, and culinary delights, Connecticut is a destination that rewards those willing to explore. Here are 18 incredible things to do that’ll give you a taste of Connecticut’s best moments (near Westbrook).
1. Eat a Lobster Roll at Bill’s Seafood (Westbrook’s Local Favorite)
Nothing says “New England” like a lobster roll, and Bill’s Seafood is the go-to spot for this regional specialty. Located just a short drive from Captain Stannard, this local gem serves up fresh, decadent lobster rolls that are the perfect blend of buttery goodness and seaside charm. Sit outside by the marina and enjoy your meal with the sights and sounds of the water.
Insider Tip: Pair your roll with their famous clam chowder for the ultimate coastal feast.
2. Climb Aboard Wooden Ships at the Mystic Seaport Museum
Step back in time with a visit to the Mystic Seaport Museum, the largest maritime museum in the U.S. This interactive experience lets visitors immerse themselves in Connecticut’s long-standing maritime history. You can explore a recreated 19th-century seaport village, watch blacksmiths at work, and even step on board the historic Charles W. Morgan, the only remaining wooden whaling ship in the world.
Planning Tip: Pair your visit with a trip to the nearby Mystic Aquarium by opting for a Mystic Seapass for access to both in one day.
3. Indulge in New Haven’s Famous “Apizza”
True pizza enthusiasts know that New Haven is a mecca for “pizza” lovers. Don’t miss legendary pizzerias like Frank Pepe Pizzeria Napoletana, Sally’s Apizza, and Modern Apizza, known for their unique Neapolitan-inspired, thin-crust pies with crispy, charred edges.
Pro Tip: For something different, try the fan-favorite mashed potato pizza at BAR.
4. Relax with a Classic Beach Read on West Beach
Just steps from Captain Stannard, West Beach is the ideal spot to settle in with a great book. Breathe in the salty air, listen to the gentle lapping of the waves, and enjoy the serenity of the Connecticut shoreline. Captain Stannard provides complimentary lounge chairs and umbrellas to kick back in ultimate comfort.
Perfect Pairing: Before your beach day, stop by Breakwater Books in Guilford to pick up a novel or two.
Dive into a world of art at the Yale University Art Gallery, which features renowned works by Monet, van Gogh, Cézanne, and Nick Cave. The museum is free and houses a rotating set of exhibitions alongside an impressive permanent collection spanning African sculptures, modern pieces, and decorative arts.
5. Take a Stroll Through Yale University
A visit to Connecticut wouldn’t be complete without exploring the historic campus of Yale University in New Haven. Highlights include the stunning Sterling Memorial Library, the Women’s Table sculpture by Maya Lin, and Hillhouse Avenue, lined with historic architecture.
Planning Note: Access to certain areas may be limited if classes are in session, so check visitor guidelines in advance.
6. Discover Masterpieces at the Yale University Art Gallery
Dive into a world of art at the Yale University Art Gallery, which features renowned works by Monet, van Gogh, Cézanne, and Nick Cave. The museum is free and houses a rotating set of exhibitions alongside an impressive permanent collection spanning African sculptures, modern pieces, and decorative arts.
7. Learn About Dinosaurs at the Yale Peabody Museum
The Yale Peabody Museum of Natural History is a treasure trove of Earth’s historical wonders. Awe-inspiring dinosaur skeletons take center stage in this cathedral-like museum, while over 14 million objects tell the story of life and evolution.
Insider Tip: Check out the nearby Kline Science Building, home to Yale’s iconic Geology Lab and Science Hill.
8. Go Birding at Hammonasset Beach State Park
Hammonasset Beach State Park boasts a two-mile stretch of sand and a salt marsh teeming with wildlife. Named a “Globally Important Bird Area” by the Audubon Society, it’s a haven for birdwatchers.
Detour: Extend your birding adventure to Rocky Neck State Park for more trails and a variety of bird species.
9. Experience a Steam Train Ride Through the Connecticut River Valley
Travel back in time with a scenic steam train ride departing from Essex Station. Complete your adventure by boarding the Becky Thatcher Riverboat for breathtaking views of the Connecticut River’s lush shores and vibrant wildlife.
10. Step Into Mark Twain’s World in Hartford
Literary enthusiasts will delight in a tour of Mark Twain’s family home. This historic house in Hartford is where the famous writer penned classics like The Adventures of Tom Sawyer and Adventures of Huckleberry Finn.
Pro Tip: Parking is ample around downtown Hartford, making it convenient to explore other nearby attractions like the Wadsworth Atheneum.
11. Explore Art History at the Wadsworth Atheneum
Immerse yourself in art at the Wadsworth Atheneum, America’s oldest continuously operating public art museum. Its collection ranges from ancient Roman mosaics to cutting-edge modern art.
12. Wine & Hard Cider Tastings at Bishop’s Orchards
Located in Guilford, Bishop’s Orchards is a must-visit destination for wine and cider enthusiasts. Explore their farm market, home to locally sourced products and their selection of wines and ciders crafted on-site. Whether you favor crisp hard ciders or robust wines, there’s something to please every palate.
Planning Tip: Check their seasonal schedule for special events like live tastings and vineyard tours.
13. Hike to Gillette Castle
Step into Sherlock Holmes actor William Gillette’s imagination with a self-guided tour of his medieval-inspired castle built in 1919 – Gillette Castle. From puzzling doors to elaborate wood carvings, this one-of-a-kind 14,000 sq ft castle is full of surprises.
14. Go Antiquing in Litchfield County
Litchfield County is known as an antiquing haven. Spend a day searching for hidden gems in small towns like Kent, Cornwall, and Woodbury, often referred to as the “Antiques Capital of Connecticut.”
15. Hit the Slopes at Mohawk Mountain
During winter, Mohawk Mountain is a must-visit for skiing and snowboarding enthusiasts. This family-friendly ski area offers lessons, rentals, and well-maintained slopes for every skill level.
16. Relax at Captain Stannard House
After a day of exploring, there’s no better place to relax than at Captain Stannard. From enjoying a book on the sun-soaked Portside deck to gathering with loved ones on the sprawling lawn, the inn offers plenty of ways to unwind. Start your mornings with a bespoke continental breakfast and end your evenings soaking in the peaceful seaside charm of Westbrook.
Guest Favorites:
Savor magical outdoor summer evenings during our “Yacht Rock Nights.”
Cozy up in reading nooks scattered throughout the inn.
17. Try Fresh Oysters at a Local Farm
Connecticut’s shoreline is famous for its oysters. Visit farms like Thimble Island Shellfish Company for tours and tastings that give you a true sense of the region’s aquaculture heritage.
18. Spend a Day on the Water
No trip to Connecticut’s shoreline is complete without venturing out onto the water. Rent kayaks to explore the local waterways, or experience a more curated adventure with these fantastic options:
- Mystic Sailing Whaler & Lobster Cruise offers a picturesque escape on the Long Island Sound. It’s perfect for soaking in the shoreline’s beauty and dining on fresh seafood.
- Thimble Island Cruise provides a 45-minute narrated ferry ride through the stunning Thimble Islands, offering unparalleled views and fascinating local history.
- Joyride Charters out of Westbrook specializes in sailing, providing unique opportunities to learn the ropes or simply sit back and enjoy the ride.
Planning Tip: These activities can fill up quickly during warmer months, so booking in advance is recommended.
Discover the Charm of Connecticut
Connecticut may not always take the spotlight, but for those willing to explore, it reveals a depth of history, nature, and culture like no other. Whether you’re indulging in a lobster roll on the coast, stepping into Mark Twain’s world, or hiking to panoramic views, you’re sure to leave with unforgettable memories.
Plan your next adventure and see all that Connecticut has to offer.
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