8 Picturesque Small Towns in Connecticut for a Weekend Retreat

Connecticut consists of a wide variety of diverse landscapes and engaging small locales perfect for a weekend departure from daily life. From the tranquil riverbanks of Essex to the wine culture of Goshen and the aquatic allure of Mystic, discover the distinct character of each location.  Read on and learn about the characteristics you might not have ever considered. The options are plenty for inviting accommodations and delightful culinary experiences that make these retreats ideal escapes from the ordinary.

Essex

If you’re looking for a quiet getaway with picturesque waterfront views, Essex may be what you are looking for. Take leisurely strolls along the riverbank and enjoy the calm ambiance. Rich in historical significance, Essex features notable landmarks that are sure to scratch the history buff’s itch. The Griswold Inn, standing as one of the oldest continuously operating inns in the United States, gives visitors a glimpse into the city's past. In the War of 1812, British forces seized control of the location, converting it into a strategic operational center. Even during the Prohibition era, the site continued to host vibrant entertainment activities for the nearby sailors. Over time, various adjacent structures were incorporated into the inn complex. Additionally, the inn gained fame as a filming location for the gothic soap opera Dark Shadows. For insights into Essex's maritime history, visit The Pratt House. The structure served as the residence for the descendants of Lt. William Pratt, who was among the initial three settlers of Essex. Last but not least, the Connecticut River Museum provides a casual learning experience for the curious history enthusiast. For a restful place to land in the evening, Griswold Inn invites guests with cozy rooms, a restaurant, and a wine bar.

Litchfield

Embraced by the beauty of rolling hills and peaceful countryside, Litchfield exudes New England elegance, captivating visitors with its awe-inspiring landscapes. The Litchfield Historic District serves as a well-maintained illustration of a classic New England village from the late 18th century. It is a perfect place for a stroll to enjoy the architecture of the era. Guests might also enjoy the White Memorial Conservation Center where there is an extensive network of 40 miles of pathways that traverse diverse woodland habitats. These trails are freely accessible to the public, encouraging non-motorized passive recreational activities such as hiking, cross-country skiing, and snowshoeing. Some areas are also open to biking and horseback riding. With more than 50 entrances, the trail system offers convenient access from various locations; for seasonal lodging, visitors may wish to consider a relaxing camping experience through the White Memorial Conservation Center as well. Alternatively, the Litchfield Inn provides modern amenities with a historic ambiance, creating a homey atmosphere. Every booking comes with a complimentary breakfast as well as refreshments, along with the availability of coffee and tea.

Goshen

Oenophiles won’t have to go far to have a weekend of local vineyard delights.  Goshen, Connecticut, has a top-rated winery of its own. Miranda Vineyard offers a taste of a budding wine culture among picturesque vineyard landscapes. The Mirandas create their artisanal wines using age-old European techniques that have been handed down from one generation to the next.

While you are visiting, you might want to stop by the Thorncrest Farm, LLC & Milk House Chocolates for some delectable sweets. Besides, what pairs better with wine than chocolate? At this family-owned and operated shop, you will find a wide array of treats, from chocolate bars to caramels to chocolate-covered fruit.

When you find yourself hungry for a hearty meal, AJ’s Steak and Pizza serves up a variety of dishes, including steak, pizza, pasta, salads, and even fish sandwiches. There is sure to be something on the menu to satisfy your appetite.

When you are looking for a place to rest at the end of the day, consider The Mary Stuart House Bed and Breakfast. Wake up to a fresh continental country breakfast each morning to start your day. The bed and

Guilford

If coastal charm is what you long for, Guilford may be an excellent place for you to a restful retreat along the Long Island Sound. Walk along the sand to the sound of water gently lapping on the shore, or enjoy a picnic at Jacobs Beach, where you will also find a children’s playground and convenient facilities.  Further inland, in the heart of the community, historic Guilford Green is a quaint space with meticulously preserved colonial homes and charming shops, such as Rock Paper Sistas, offering handmade coastal crafts. Leisurely explore the past at the Henry Whitfield State Museum, a testament to history as the oldest house in Connecticut.

To keep yourself fed, there are so many establishments from which to choose, such as Prime on Whitfield for exceptional steak dinners or South Lane Bistro for farm-to-table dishes. For classic café-style cuisine at the harborside, visitors might be interested in  Pa’s Place.

When it comes to places to stay the night, visitors may consider The Guilford Mooring, a waterfront haven that provides rooms with scenic views. Alternatively, the B&B at Bartlett Farm offers a cozy farmhouse retreat, ensuring a comfortable and memorable stay.

Washington

Embraced by rolling hills and adorned with horse farms, Washington, Connecticut, is the epitome of a bucolic, soothing atmosphere. Perhaps you will want to wander through the untouched beauty of Steep Rock Preserve. You will find hiking paths of every level of difficulty leading to a 776-foot elevation overlooking the Shepaug River Valley.

Washington also thrives as an artistic community, attracting numerous creatives to its inspiring surroundings. Delve into the world of art by visiting the Washington Art Association and Gallery, a hub for creative expression.

For those seeking a retreat into luxury, the Mayflower Inn & Spa presents the perfect opportunity. This accommodation promises a pampering escape amidst the tranquil surroundings. Otherwise, if a homier experience is what you are craving, the Windemere Bed and Breakfast is just 5 minutes up the road from the center of Washington in the tiny village of New Preston. The B&B sits proudly atop a hill overlooking the rolling countryside.

Suffield

Suffield presents a delightful getaway for the history enthusiast. The past comes alive in the town's center, a focal point with colonial architecture lining the streets. Notably, the Phelps-Hatheway House and Garden is a popular attraction. Visitors can take a personal look into the lives of 18th-century families who once lived in the home.

For those who prefer nature, guests of Suffield will find scenic parks that encourage exploration. Sunrise Park, with its panoramic views of the Connecticut River, has so much to offer the traveler. For example, there are walking paths, swimming areas (one specifically for dogs), and fishing areas.

When you have worked up an appetite after a day of activities, consider the Three Figs Restaurant for dinner. There is something there for everyone, from burgers to vegetarian dishes. If you are in the mood for Mediterranean-inspired food, you might want to try Tosca. Some of their featured fresh pasta dishes are Lobster Ravioli and Beef Short Rib Ragu.

For those yearning for a truly relaxing place to land for the night, book a room at the Lily House Inn for a massage and a restful sleep.

Kent

If art is your passion, Kent might be a great place for a respite. Just 2 hours away from New York City, the small town of 3015 inhabitants has a surprising number of art galleries, with at least six, according to the Kent Chamber of Commerce web page. The Kent Art Association is just one such cultural delight, offering an enriching dose of artistic expression.

For nature enthusiasts, Kent presents a retreat into the serene embrace of its natural wonders. Kent Falls State Park is well known for its series of waterfalls, creating a captivating backdrop for woodland adventures. Meanwhile, Macedonia Brook State Park invites hikers to traverse its trails along the falls. Visitors should be aware that while the trail is not known for a high level of difficulty, it is steep. The reward for the climb undoubtedly is worth the surrounding unveiling landscapes.  Or perhaps when the weather permits, a mini camping vacation would be your style. In that case, Macedonia State Park has you covered. There, you will also find fishing and hiking areas.

When it comes to inside accommodations, the Fife 'n Drum consists of not only an inn but also a restaurant serving a wide variety of dishes, from roast duck to a variety of vegetarian dishes. 

Mystic

Mystic is situated on the shores of the Long Island Sound, making an excellent locale for an aquatic-themed getaway. One of its prominent attractions is Mystic Seaport Museum, renowned as the nation's leading maritime museum, offering visitors a captivating journey through maritime history. Mystic Aquarium provides an immersive experience, allowing interaction with a variety of sea creatures.

For shopping and dining, take a leisurely stroll through Olde Mistick Village, a gathering, shopping, and dining area. It was built to resemble a 1720-style colonial village, complete with a village green and a duck pond.

When it comes to lodging in downtown Mystic, The Whaler's Inn provides a boutique hotel experience with comfortable and convenient provisions and an on-site restaurant. Continuing the nautical theme, The Steamboat Inn, situated along the Mystic River, offers a unique and intimate stay.

Embark on a Picturesque Retreat in Connecticut

Whether you seek historical immersion, coastal tranquility, artistic expression, or natural wonders, these destinations call with a promise of unique experiences. So, go ahead and savor what Connecticut's diverse communities have to offer, promising a memorable escape filled with history, nature, and cultural exploration. Each municipality invites you to become a part of its fabric, even if it is only for a couple of days. Which place will you visit for your next weekend away? And your next? With so many from which to choose, why not explore them all?