8 Coolest Towns in Connecticut for a Summer Vacation in 2024

One of the original 13 American states and a member of the six New England states, Connecticut is an Atlantic state with borders along Massachusetts, Rhode Island, and New York. The state sees a true four-season climate with somewhat cold and snowy winters and nice warm summers. Connecticut is known for its beaches and scenic green forests, and is rich with history and contemporary arts and culture. Whether looking for a romantic getaway in a cute historic town or an adventure-filled camping trip, Connecticut is a cool spot for a summer vacation in 2024.

Middletown

Home to seven walkable blocks in its downtown core, 200 independent businesses, and a dozen different cuisines, Middletown is a quintessentially Connecticutian town perfect for a summer getaway. The National Trust for Historic Preservation has named the town one of the US's most romantic. Middletown is home to Wesleyan University as well as the Wesleyan Potters, Oddfellows Playhouse Youth Theatre, and the Davison Art Center. While in town, consider a day trip to the Wadsworth Falls State Park or the Brownstone Adventure Sports Park.

This summer, the Middlesex County Historical Society is hosting the A Vanished Port—Middletown & the Caribbean, 1750-1824 exhibit, which explores Middleton's history of enslavement, wealth, and commerce in the 18th and 19th centuries. One of the best places to stay in town is the Inn at Middletown, which offers old New England accommodations and charm.

Southington

Southington is an eclectic and vibrant Connecticut community known for its three challenging public golf courses and Lake Compounce, the US's oldest continuously run amusement park. In the summer, spend the day walking around downtown and visiting the Barnes Museum and the Southington Community Cultural Arts Center, and at night, head to the Southington Drive-In.

There are a couple of major hotel chains in town, such as Residence Inn and Holiday Inn, but Airbnbs are also widely available, and there are numerous charming accommodations available. Castle Craig and Hubbard Park are excellent spots to get outside near town and are worthy of making the day trip. On Wednesdays throughout the summer, visit Southington Town Green for the Music on the Green concert series.

Groton

Located on Fishers Island Sound, Groton is primely situated between green forests, hills, and sandy beaches. As the submarine capital of the world, Groton is known for its historical sites and rolling shoreline. Some of the best activities nearby include visiting the New London Soldiers & Sailors Monument and Veterans' Memorial Park, the Salmon River State Forest, and the Mohegan Park and Memorial Rose Garden, all within a short drive from town.

While in town, visit Fort Griswold Battlefield State Park to soak in Groton's history, as well as the nearby Mystic Seaport Museum and New London Ledge Lighthouse. One of the nicest places to stay in town is the Hampton Inn Groton, though there are countless stay options that will adhere to your budget and needs. On Fridays throughout the summer, attend one of the Concerts in the Park at Washington Park, where there are several food trucks, concession stands, and dancing space available.

Torrington

Torrington is an ideal vacation spot for those looking to spend a weekend on a vineyard. The downtown is known for its shopping and cultural centers, such as the Warner Theatre, Torrington History Museum, and Hotchkiss-Flyer House Museum. Some of the best bites in town include Geppetto-Osteria E Bisteccheria, The Venetian, and YiaYia's Greek Kitchen.

The best vineyard in the area is Sunset Meadow Vineyards and no visit to Torrington is complete without visiting the Action Wildlife Foundation. There are numerous major-chain accommodation options in town to suit your needs such as a Days Inn.

Vernon

Full of museums such as the New England Civil War Museum and the New England Motorcycle Museum, Vernon is a small Connecticut town with ample to do. Near town, the Valley Falls Park, Belding Wildlife Management Area, and Henry Park offer excellent and beautiful outdoor recreation. Vernon is also home to a number of delicious eateries, including Angellino's, Between Rounds Bakery Sandwich Cafe, and Elmo's Dockside Restaurant.

There are only a few accommodation options, including a Travelodge, Holiday Inn, and Days Inn, so booking in advance of peak tourist seasons is recommended. Whether you are just passing through or staying to explore the town, sit down for a local bite at Frankie B's Tavern or Wood-n-Tap.

Branford

Known for its rocky shoreline, Branford is a great quiet summer destination for those eager to be on the water. For those visiting from out of town, Branford River Paddlesports, Kayaks, and Tours, as well as Nightjack Sportfishing, will help get you out on the water in your preferred recreational method. While in town, the Thimble Island Brewing Company and Los Charros Cantina are some of the best spots to refuel after a day on the water.

The Goodsell Point Marina and Safe Harbor Bruce & Johnsons hotels overlook the town's waterfront, offering great views from your room morning through night. The nearby Farm River State Parks offer beautiful hiking trails year-round. From June 27 to 28, the Branford Jazz Festival will fill the air with live music throughout town.

Rocky Hill

A jumping-off point for sailors, boaters, and swimmers eager to spend time in and on the Connecticut River, Rocky Hill is a must for any Connecticut summer vacation. Rocky Hill boasts the Dinosaur State Park, Rolling Greens Golf Course, Rocky Hill-Glastonbury Ferry, and the Academy Hall Museum. The Sheraton is arguably the nicest place to stay in town though there are numerous accommodation options available in and around the area. From July 9 to 10, the Rocky Hill Summer Concert Series will take over the Veterans Memorial Amphitheatre.

Seymour

Known for its beautiful but small historic district, Seymour is a small river town full of local family farms. The Seymour Antiques Company offers some world-class antiquing that attract visitors from across the globe. The Inn at Villa Bianca is a cute place to stay for the weekend, right on the Housatonic River. To make the summer vacation complete, a day trip to the Indian Well State Park, Osbornedale State Park, or Lake Zoar is an absolute must when visiting Seymour. On select nights throughout the summer, the Great Hill Hose Co. is hosting Audacity - Seymour Culture & Arts Concert Series for the second year in a row.

Connecticut is a beautiful but small New England state full of eclectic and historic small towns and villages worth exploring. A coastal state, many of the communities throughout Connecticut are reliant on or based on river, lake, and ocean culture. Whether you are eager for a romantic getaway, a long weekend with the whole family, or a secluded community to escape to for a month in the summer, Connecticut undoubtedly has the coolest vacation spot to spend part of 2024's summer exploring.