A Guide To The Perfect Weekend in Connecticut
Connecticut, often overlooked by travelers on their way to New York or Boston, is a treasure trove of charming towns, scenic landscapes, rich history, and diverse attractions. One of the benefits of visiting a small state like Connecticut is that visitors will spend minimal time travelling between attractions and maximal time enjoying the state. If you are looking for a weekend getaway full of variety, this itinerary will help you craft the perfect road trip through the Constitution State. Start your Connecticut road trip in New Haven, accessible via Amtrak or Metro North train, Airplane to Tweed New Haven Airport, or motor vehicle via Interstate 95 or Interstate 91.
New Haven
New Haven is known for its academic atmosphere, historic sites, and vibrant arts scene. Begin with a visit to Yale University, one of the oldest Ivy League schools in the nation. Its stunning campus is a mix of Gothic architecture and modern designs. As you walk around, you’ll be impressed by the Harkness Tower and the Sterling Memorial Library, both of which offer an air of grandeur. Yale also boasts world-class museums, with the Yale University Art Gallery being a must-see. The gallery offers a diverse collection, from international works throughout human history to modern pieces, and entrance is free of charge.
After soaking in the art, take a stroll to the New Haven Green, a 16-acre public park at the heart of the city. Surrounded by historic churches and 19th-century buildings, the Green is where New Haven was originally founded in 1638. It's the perfect place to take a break, admire the beautiful landscape, and learn about the city’s colonial past. For lunch, make sure to stop by Wooster Street for one of New Haven’s famed pizzerias. Frank Pepe’s Pizzeria Napoletana and Sally’s Apizza date back to 1925 and 1938 respectively, for an authentic slice of authentic, brick oven-baked New Haven-style pizza, in its crispy, charred (do not call it burnt) thin crust glory, a small taste of the divine, annually voted among the best in the country.
After lunch, continue your journey with a short drive to Lighthouse Point Park, located along the shores of Long Island Sound. The park is a favorite among locals and tourists alike, with its beach, boardwalk, and its seasonally operated antique carousel. This peaceful place to unwind offers lovely panoramas of downtown New Haven and views of the sound, and the historic lighthouse on site has been standing for over a century. If the weather is nice, spend some time walking along the beach or simply relax and watch the sunset over the water, a perfect way to end the day.
Madison
After a fulfilling day in New Haven, head southeast to the charming town of Madison, where you can find a cozy place to rest for the night. The Madison Beach Hotel, located just a short 20-minute drive from New Haven, is an excellent option. This boutique hotel offers a relaxing atmosphere and stunning views of the Long Island Sound, making it a peaceful retreat after a full day of exploring. The hotel’s proximity to the beach also means you can enjoy a walk along the shoreline before calling it a night.
Mystic
On day two of your Connecticut road trip, head out to explore more of the shoreline and the rich history of the state. Start your day by continuing eastward to the coastal town of Mystic, a little under an hour’s travel by train or car away from Madison. Mystic is best known for its maritime heritage and charming New England feel. Your first stop in Mystic should be the Mystic Seaport Museum, one of the largest maritime museums in the world. This museum brings history to life with its historic ships, restored buildings, and fascinating exhibits about the region’s seafaring past. You can explore old whaling ships, learn about shipbuilding traditions, and even board some of the vessels that once sailed the seas. The museum is a great stop for families or anyone interested in American history.
After spending the morning at Mystic Seaport, take a short drive to the downtown area, where you can visit the Mystic Aquarium. Known for its excellent collection of marine life, the aquarium offers interactive exhibits, including a chance to see beluga whales, sea lions, and penguins up close. It’s a fun and educational experience for all ages. For lunch, enjoy some fresh seafood at one of the local restaurants in downtown Mystic, such as the S&P Oyster Co., which overlooks the Mystic River. Their lobster rolls are a local favorite.
In the afternoon, make your way to the Olde Mystic Village, a charming shopping area that features colonial-style buildings, boutique shops, and cafes. As you wander through the village, you’ll encounter lovely little shops selling everything from handmade candles to jewelry and local art. It’s a great spot to pick up unique gifts, enjoy a beer at the Jealous Monk, and take in Mystic’s quaint atmosphere. Keep in mind that some Village attractions operate seasonally, so take this into account if you're planning a weekend trip in Connecticut during off-peak months.
In the evening, you can stay in the town of Mystic at one of its charming bed-and-breakfasts or inns, such as the Whaler’s Inn. Located just steps from the Mystic River, this cozy inn offers a comfortable stay and is within walking distance of the town’s restaurants, shops, and attractions. Enjoy a relaxing evening and a delicious dinner at one of the nearby restaurants like the Engine Room, featuring views of the river. Don’t forget to sneak in a nightcap at one of the nation’s oldest pubs, the Daniel Packer Inn, before getting a good night’s rest.
Haddam, Hartford, and Beyond
On your final day in Connecticut, you’ll explore the more rural areas of the state. Begin your morning with a visit to the Gillette Castle State Park, a marvelously luxurious stone mansion located in East Haddam. The castle, which first served as home to stage actor William Gillette, most famous for his portrayals of Sherlock Holmes, was built between 1914 and 1919, and is perched on a hill overlooking the Connecticut River. The unique structure, with its medieval-style architecture, is unlike anything else in the state.
Take a guided tour through the castle, where you’ll learn about Gillette’s life and eccentricities. The surrounding park offers hiking trails with stunning views of the river and a chance to explore the lush forests and scenic landscape. After visiting the castle, head to the nearby village of Hadlyme for a ride on the Connecticut River Ferry. This historic ferry ride will take you across the Connecticut River, providing beautiful views of the river and the surrounding countryside. It’s a fun way to experience the natural beauty of the region.
In the afternoon, make your way to the town of Hartford, Connecticut’s state capital. Hartford is rich in history and is home to the Mark Twain House & Museum, the former residence of the famous author. The house, which was built in the 1870s, offers guided tours that take you through the rooms where Twain lived and wrote some of his most famous works, including The Adventures of Tom Sawyer and Adventures of Huckleberry Finn. The museum provides fascinating insights into Twain’s life, his writing career, and his impact on American literature.
Before wrapping up your road trip, take a stroll through Hartford’s Bushnell Park, a historic green space in the heart of the city. The park offers walking paths, ponds, and beautiful views of the state Capitol building with its beautiful gold dome shimmering in the fading sunlight. It’s a relaxing place to unwind after a busy day of sightseeing. As your weekend road trip comes to a close, you’ll have experienced the best of what Connecticut has to offer, from its historic towns and charming coastal views to its rich cultural landmarks. Connecticut’s diverse attractions will leave you with lasting memories and a desire to return for another road trip soon.
