7 Best Towns In Connecticut For A Two-Day Recharge

Summer is well underway, and it seems like everyone is heading off on vacation. If you are craving a getaway of your own but cannot commit to a full week away, don’t fret! Connecticut has plenty of towns perfect for a quick weekend recharge. These seven spots are not only beautiful but also small enough to explore without feeling overwhelmed. Towns like Westport are filled with beaches, while other towns, like New Canaan, are filled with artsy museums and historic inns. So pack your weekend bag and get ready for a short, satisfying escape.

Mystic

If your ideal weekend is spent on the water, Mystic has the perfect attractions for you. Travelers can kick off their weekend with a stay at Harbor View Landing, a waterfront property with newly built Captain Homes and luxury cottages. The next morning, get ready for a boat tour with Mystic Boat Adventures, which offers three-hour, comprehensive tours of landmarks like the Mystic Drawbridge, local lighthouses, and Fishers Island Sound. If you prefer something a little bit slower, you can rent a kayak or paddleboard with Adventure Mystic, a local rental agency that lies along the Mystic River. They also offer occasional themed paddle tours, such as a Jawsfest paddle and a Full Moon Paddle Tour for something a bit different!

Westport

If you are seeking a weekend on the beach, Westport should be at the top of your list. This town has four beaches within city limits, with Sherwood Island State Park being one of the most popular. This state park spans over 235 acres, boasting plenty of shoreline for sand castle building or sunbathing. Once the sun starts to set, head over to The Whelk for dinner, which serves sustainable seafood in a casual atmosphere. Some of the entrees you may be able to order include striped bass, squid ink cavatelli, and lobster orecchiette. Regarding accommodations, The Inn at Longshore is a highly rated hotel in the area, featuring 12 cozy rooms with a mix of antique and modern furnishings.

Madison

In addition to being a beloved beach town, Madison is also a hub for agritourism. One example is Field House Farm, a local farm that periodically hosts field-to-table dinners. Each event begins with a tour of the farm, followed by an introduction from the chef and wine expert, and concludes with a fresh, multi-course meal. If you are eager for more local food, stop by Madison’s weekly farmers market, held every Friday from May through Thanksgiving, between 3:00 and 6:00 p.m. After a day on the beach or at the farm, unwind for the evening at the Scranton Seahorse Inn, which is housed in a beautiful 1833 Greek Revival home.

New Canaan

Rich in art and culture, New Canaan is home to several distinctive museums that belong on every museum lover’s itinerary. The Glass House is the first, constructed between 1949 and 1995 by famous architect Philip Johnson. In addition to appreciating its architecture, visitors can browse a permanent collection of 19th-century sculptures and paintings on the property. Afterward, make your way over to Grace Farms, a cultural and humanitarian center that has rotating exhibits highlighting themes like community, justice, faith, arts, and nature. After a day of museum hopping, relax at the Roger Sherman Inn, an 18th-century home that features 17 unique guest rooms and suites.

Kent

Surrounded by rolling hills and waterfalls, the small community of Kent fosters a thriving art scene that reflects its natural beauty. Travelers can start their afternoon by visiting Kent Falls State Park, famous for its red covered bridge and 250-foot cascades. Afterwards, head back into town to visit some local galleries. The Morrison Gallery is a must-visit for your itinerary, a recently opened gallery that exhibits artwork from national and international contemporary artists. Visitors can get an even better sense of the town’s personality by staying at one of the Kent Collection properties, which include a Victorian-style home, a cozy inn, and charming garden cottages.

Essex

With a colonial history that dates back to 1635, Essex is filled with maritime heritage and history. Travelers can experience a piece of this heritage aboard the Essex Steam Train & Riverboat, which offers two-and-a-half-hour narrated tours that begin on a steam train and continue on a Mississippi-style riverboat. The Connecticut River Museum is another great stop, located along the river and offering historical exhibits that cover 12,000 years of the area’s history. The museum also features two vessels: a recreated Dutch yacht based on a 1614 design, and a research vessel used for river tours focused on local wildlife. Conclude your historical experience with a stay at the Griswold Inn, which is one of the country’s oldest continuously operating inns, established in 1776.

Old Saybrook

Located at the intersection of the Connecticut River and Long Island Sound, Old Saybrook is a laid-back, seaside community that offers the perfect change of pace. In the summer, the Old Saybrook Town Beach is a popular place to spend the afternoon, staffed with lifeguards from Memorial Day until Labor Day each year. Saybrook Point Miniature Golf Course is another great outdoor activity, a waterfront mini golf course that is positioned along the mouth of the river. Travelers can also stop by the Lynde Point Lighthouse a prominent, white lighthouse along the shores that dates back to 1886. For a luxurious night’s sleep, consider lodging at the Saybrook Inn. The inn’s main hotel has 82 guest rooms, many of which have views looking out over the water, and an on-site spa.

Final Thoughts

Thanks to Connecticut’s compact size, even a weekend is enough to reach just about any corner of the state. If you are hoping to spend the weekend on the coast, towns like Old Saybrook, Westport, Mystic, and Madison await. Wanting to cool off indoors? Pick a town like New Canaan, Kent, or Essex, and visit their galleries and museums. No matter how you choose to spend your weekend, you are sure to return feeling recharged and ready to take on the world again.