The Best Day Trips From Connecticut

Connecticut is one of America’s smallest states, but that shouldn’t fool anyone. Its small stature belies the many exciting day trips at its borders. Options include bustling metropolitan cities like Boston and New York, easy-on-the-eye getaways at Hopkins Vineyard, Newport or Hyannis, and unusual spots like the Old Sturbridge Village living museum. If you need help choosing, check out our list of the best excursions from Connecticut.

Did you know – Culture Trip now does bookable, small-group trips? Pick from authentic, immersive Epic Trips, compact and action-packed Mini Trips and sparkling, expansive Sailing Trips.

New York City, NY

Building, Museum, Park

Depending on where you are in Connecticut, New York City can be anywhere from two hours to a mere 45 minutes away. Take a train into Grand Central and start your visit admiring this elegant station with its iconic clock atop the information booth and the constellation-covered ceiling. From there, walk over to the public library guarded by stone lions and relax in Bryant Park, before heading downtown to the towering Empire State Building. After a lunch of classic New York pizza, brave the subway to Battery Park, where cruises sail past the impressive Statue of Liberty. Finish the day admiring the lights and billboards in Times Square before taking in a show on Broadway.

Hopkins Vineyard, New Preston, CT

Winery
Overlooking Lake Waramaug, the vineyard is located in the hills of scenic Litchfield County and has been owned by the Hopkins family for 225 years. The proximity to the lake has a very interesting effect, creating a micro climate that allows it to extend its growing season and produce grape varieties that would normally not flourish in this region. Hopkins grows 11 varieties of grapes, producing reds, whites and sparkling wines. Guided tours explain the grape-growing and wine-making process, and tastings allow samples of wines along with recommendations and suggestions for food pairings. The cosy wine bar is located in the hayloft of the 19th-century barn with views over the lake, and visitors can sample the wines with cheeses, fresh bread and pâté.

Newport, RI

Architectural Landmark, Natural Feature
Less than two hours from Connecticut is the pretty coastal city of Newport, the sailing capital of the world. Newport is famous for its historic grand mansions, so start the day with a tour of one on Bellevue Avenue. Then take a scenic hike along the paved 3.5mi (3.6km) Newport Cliff Walk, admiring the rugged coastline, cliffs and more mansions. Historic Thames Street, running along the waterfront, is the main thoroughfare for shopping and also has a mix of restaurants, lively bars, museums and notable churches. Finish the day with a sunset dinner at one of the many restaurants overlooking the water.

Boston, MA

Architectural Landmark, Historical Landmark

The wicked city of Bahston is the capital of Massachusetts and approximately two hours from Connecticut. Start the day in the popular Boston Common and spend some time following the Freedom Trail. Follow it to Quincy Market, a giant food hall, and grab something to snack on while overlooking the marina in Christopher Columbus Waterfront Park. The next stop is the historic Paul Revere House, a 17th-century home overlooking a cobbled square; touring the small property shouldn’t take more than an hour. Finish the afternoon shopping in Back Bay along Newbury Street.

Old Sturbridge Village, MA

Museum, Historical Landmark

Old Sturbridge Village is a unique attraction. At 200 acres (81ha), it is New England’s largest living museum and recreates rural life from the 1790s to the 1830s. It has 40 restored antique buildings, moved from various locations, and is divided into three areas: the Common and Center Village, the Countryside, and the Mill Neighborhood. Visitors can explore the village, wandering into spaces such as the blacksmith shop, cider mill or Thompson Bank where costumed, trained historians will educate and answer questions on life in the 19th century. Visitors can enjoy ice cream or eat in the tavern and shop in a number of stores. Tickets can be purchased online.

Hyannis, Cape Cod, MA

Architectural Landmark, Historical Landmark
On the south peninsula of Cape Cod is the vibrant town of Hyannis. It first gained fame as the summer home of John F. Kennedy, also known as JFK, during his presidency, and has hosted Kennedys for generations ever since. Visitors will find a monument to JFK at Lewis Bay, the JFK Museum and the Kennedy Legacy Trail, which highlights sites of significance to the family. The coastal town is a bustling, popular destination, with plenty to keep visitors busy: lounging at sandy Craigville Beach, seafood at the Naked Oyster, shopping on Main Street, art galleries, and plenty of opportunities to get out on the water with cruises from Lewis Bay or kayak rentals.

Since you are here, we would like to share our vision for the future of travel - and the direction Culture Trip is moving in.

Culture Trip launched in 2011 with a simple yet passionate mission: to inspire people to go beyond their boundaries and experience what makes a place, its people and its culture special and meaningful — and this is still in our DNA today. We are proud that, for more than a decade, millions like you have trusted our award-winning recommendations by people who deeply understand what makes certain places and communities so special.

Increasingly we believe the world needs more meaningful, real-life connections between curious travellers keen to explore the world in a more responsible way. That is why we have intensively curated a collection of premium small-group trips as an invitation to meet and connect with new, like-minded people for once-in-a-lifetime experiences in three categories: Culture Trips, Rail Trips and Private Trips. Our Trips are suitable for both solo travelers, couples and friends who want to explore the world together.

Culture Trips are deeply immersive 5 to 16 days itineraries, that combine authentic local experiences, exciting activities and 4-5* accommodation to look forward to at the end of each day. Our Rail Trips are our most planet-friendly itineraries that invite you to take the scenic route, relax whilst getting under the skin of a destination. Our Private Trips are fully tailored itineraries, curated by our Travel Experts specifically for you, your friends or your family.

We know that many of you worry about the environmental impact of travel and are looking for ways of expanding horizons in ways that do minimal harm - and may even bring benefits. We are committed to go as far as possible in curating our trips with care for the planet. That is why all of our trips are flightless in destination, fully carbon offset - and we have ambitious plans to be net zero in the very near future.