8 Connecticut Weekend Getaways for Seamless Stays in the Nutmeg State

From all-seasons outdoor activities to designer shopping and fine dining, here are the 8 best destinations for fun Connecticut weekend getaways.

Connecticut may be the third smallest state in the country, but it’s far from short on adventure. From an abundance of natural beauty surrounding dozens of small towns packed with history and charm to its bigger cities crammed with culture, settling on your exact destination here will be far more difficult than filling your itinerary. Whether you’re destined for designer shopping, pining for pizza, hankering for historical immersion, or needing nature, it’s all here in the Nutmeg State. This list will help you on your quest to identify the best Connecticut weekend getaway for you. Feel free to try them all!

Mystic: Celebrate the seafaring life


It may no longer be the maritime powerhouse it was in the 18th and 19th centuries, but visits to Mystic remain centered around the river of the same name.

Grab some sandwiches for a picnic lunch at Mystic Market and charter a sailboat for a private day on the water. Head toward Fisher’s Island (feel free to snorkel and dive around the island in warmer months); if you’re up for a bit more adventure, continue out into the Atlantic Ocean before turning back in the early afternoon. You’re unlikely to spot beluga whales from your sailboat, but you can always catch them in their outdoor habitat at the Mystic Aquarium, widely considered the best in the state.

For dinner, take your pick from a plethora of incredible seafood restaurants around town; if you’re celebrating a special occasion, Oyster Club is a solid bet for an upscale meal in a chic but unfussy interior, with a deck available for al fresco dining. It’s right by the Mystic Museum of Art, in case you need a little break from maritime madness.

You’d be missing the point of Mystic if you skipped the Mystic Seaport Museum, where you’ll learn the history of the town’s shipbuilding and seafaring past, tour the Seaport Village, and explore historic boats and ships. The museum also operates one of the town’s most popular attractions, Sabino Steamboat, offering river cruises on one of the world’s last operational coal-fire steamboats.

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Where to Stay

Ideal for a quiet couples weekend, the Inn at Mystic offers the only accommodations overlooking Mystic Harbor and Fisher’s Island Sound. Get that country inn feel within any of the Inn’s 52 nautically-inspired rooms. Enjoy lobster stuffed avocados for dinner on the deck of Rocks 21, the Inn’s onsite restaurant, or just stop by to pick at the $6 happy hour menu as the sun sets. You’ll find a walking trail and formal gardens for quiet strolls on the property, but the Inn’s best and most romantic features are the Jacuzzi tubs and fireplaces found in most rooms.

Inn at Mystic

8.0 Very good (59 reviews)

Chester: Find historic charm


When you’re searching for Ye Olde America, choose Chester, Connecticut. This idyllic town dates to 1692 and is devoted to preserving and promoting its colonial heritage.

Around town you’ll find half a dozen well-preserved historic houses (and a 19th century bank), but most of the action is centered on Main Street, which is every bit as charming as you’d hope. Grab a gourmet deli lunch at Simon’s Marketplace before spending the afternoon admiring dozens of art galleries and jewelry studios in town and snagging some souvenirs and gifts at R. J. Vickers Herbery.

Afterward, catch a show at The Terris Theatre on Main Street, hosting presentations from Goodspeed Musicals, an organization whose primary stage is at the riverfront Goodspeed Opera House ten minutes outside of town in East Haddam.

For a small break from consuming all of Chester’s quaint culture, head just outside town’s borders for generally easy hiking trails in East Haddam favorites like Brainard Homestead State Park and Cockaponset State Forest.

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Sophisticated travelers who have come to town for Chester’s charms should check in to Boardman House. Behind its grand entrance, this 1860 Second Empire mansion presents historical elegance at every turn, with antique furniture and fine textiles outfitting each stately room. However, modern upgrades like air conditioning and heated marble floors will keep you in the comfort of the present day. Less than a quarter mile from the river and area restaurants, you can be in or out of the action as easily as you like here.

Boardman House Inn Bed & Breakfast

Top rated
East Haddam
8.8 Excellent (28 reviews)

New Haven: Harness high culture


Some will try to convince you that Yale University isn’t the only game in town, but don’t listen to them. Sure, they may be literally correct, but they’re culturally wrong. Since its inception, Yale and New Haven have been inextricably linked as the city developed its highbrow culture around the academia of one of the country’s top universities.

Spend a day popping in and out of museums, choosing from an extensive menu of Yale offerings including Yale Peabody Museum of Natural HistoryYale University Art GalleryYale Center for British Art, or even the school’s Sterling Memorial Library, with impressive architecture and design that’s free to enter and admire.

If your Connecticut weekend getaway is a long one and extends through Tuesday night, you can also stop into the storied Leitner Family Observatory & Planetarium (also part of Yale) for a public show and a chance to use some of the equipment.

Between browsing all things Yale, turn to that culinary favorite of every college student – pizza, but understand that New Haven-style pizza is called “apizza.” It’s a super crispy, considerably smudgy, coal-fired, thin crust Neapolitan pie that originated either at Frank Pepe or Sally’s Apizza and is now popular citywide (and beyond).

Beyond pizza, you should also grab a hamburger from the spot where it was invented, Louis’ Lunch.

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Fully embrace the theme of your New Haven visit by signing up for a stay at The Study at Yale. This small chain of quirky boutiques welcomes guests to university towns with design and décor that highlight local collegiate life, but with an atmosphere closer to the dean’s house than a frat house. Page through the library collection in The Study’s living room as you plot your day—all of Yale’s main attractions are just minutes from the hotel—but be sure to check out the property’s own rotating collection at the Aisling Gallery, featuring the artwork of Yale students.

The Study at Yale, Study Hotels

Top rated
New Haven
9.4 Excellent (835 reviews)

Essex: Take a ride into the past


History buffs of all kinds will appreciate the yesteryear charm of peaceful Essex, but those with a particular interest in transportation history will be especially tickled. Hop aboard the Essex Steam Train for a narrated sight-seeing tour of similarly scenic neighboring towns, or spring for the 2.5-hour combo tour that also includes a riverboat cruise on the triple-decker Becky Thatcher. The train tour explores natural preserves and coves nearly inaccessible otherwise for a unique eco-experience, while the river cruise highlights some of the region’s most famous landmarks with views from their best vantage points.

Back on foot, Downtown Essex is renowned for its small-town appeal. It features plenty of historical houses and buildings, some of which date back to the Revolutionary War period, as well as a host of boutiques, galleries, and restaurants. Connect with Essex’s boating history at the Connecticut River Museum and, if you haven’t had enough train time yet, you can always head back to the station for reservations on the Essex Dinner Clipper Train, serving four elegant courses on a 2.5-hour roundtrip journey.

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Settle in to the Bee and Thistle Inn in nearby Lyme for a cozy base for your Connecticut weekend getaway in Essex. Each of the 10 guestrooms at this 1756 bed and breakfast comes with a private bathroom and includes a hearty country-continental breakfast. Lyme is an artistic town with plenty of additional galleries and studios to admire in addition to your Essex exploration, but the Bee and Thistle Inn brings the town’s artistic spirit directly to you with its own collection of sculpture, painting, photography and more filling both the Inn’s rooms and grounds. Admire, inquire, or even purchase pieces from this de facto gallery.

Bee and Thistle Inn and Spa


Cornwall: Explore the outdoors in all seasons


It’s Mohawk madness in scenic Cornwall. In winter, Mohawk Mountain has been a popular destination for skiers since the 1940s, offering both day and night skiing and snowboarding, plus recently-added snowtubing for those who want to enjoy the powder with less of a workout.

In warmer months, the rest of surrounding Mohawk Mountain State Forest State Park takes center stage with hiking, camping and both pond and stream fishing. The state forest/park combo is home to an impressive wildlife sanctuary and Black Spruce Bog, a presumed glacial sink hole that has fostered a unique plant community worth witnessing.

For winter fun for those not interested in ascending the mountain, some forest/park trails are designated for snowmobile use when covered by at least six inches.

Believe it or not, Cornwall’s most famous symbol isn’t the mountain, but its exceptional covered bridge (one of only three remaining in the state). It’s a favorite destination for picnics, strolls, and social media mavens – especially in the fall when the surrounding leaves add a magnificent backdrop of colorful bliss. Consider a rental from Covered Bridge Electric Bike for some all-seasons light adventure here and beyond.

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Head a bit out of town (about 20 minutes) for a stay at Interlaken Inn Resort & Conference Center. The property is flanked by a pair of lakes offering a bounty of aquatic activity, like canoeing and kayaking with free rentals from the resort, swimming, fishing, and sailing. For fresh air on foot, Interlaken Inn boasts 30 acres rife with scenic strolls and is also home to impressive sculpture gardens professionally maintained by Salisbury Garden Center. Morgan’s Restaurant is popular with area residents and guests alike for its seasonal menu of farm-to-table fare, and Ellora Spa provides a full-service menu of massages, treatments, and yoga and Pilates classes. Resort guests can even receive select treatments in their room.

Interlaken Inn Resort & Conference Center

8.0 Very good (61 reviews)

Greenwich: Hobnob with the hoi polloi


Greenwich benefits from its fabulous combination of exquisite countryside landscape and close proximity to New York City, making it a magnet for the finance capital’s wealthiest families. While you may not be able to afford one of this prominent town’s multi-million-dollar estates, you can take a peek behind the curtain of the 1% lifestyle with a Connecticut weekend getaway here.

Indulge in designer shopping in Downtown Greenwich, where you’ll find familiar luxury shops like Saks Fifth Avenue and Brooks Brothers, but look for its more eclectic offerings, like the ogle-worthy luxury disguises at Sophia’s Costume Rentals & Gift Shop and the masterful silver and metalwork at Michelangelo.

Chic dining options include Italian at Terra Ristorante and French at Bistro Versailles, and there’s more jewelry and art than you can imagine in this tiny town.

Opulence aside, return to nature with a visit to the Greenwich Audubon Center. Here you’ll find 285 acres of natural sanctuary with tranquil trails spanning 7 miles, a vernal pool, hardwood forest and the informative Kimberlin Nature Education Center. If you’re brought kids on this getaway, they’ll especially enjoy the interactive Nature Play Trail here.

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It’s only fair that you get to surround yourself with a little luxury for your overnights in Greenwich, so unpack your bags at Homestead Inn – Thomas Henkelmann. This boutique hotel is home to sophisticated guestrooms with European flair and surrounded by a lush landscape of mature trees lining pristine lawns, overflowing flowerbeds, and stately topiary. The Inn’s crown jewel is the Thomas Henkelmann Restaurant, showcasing the renowned chef’s fine French menu for lunch and dinner and offering a room service menu to the Inn’s pampered guests. Everything you desire from a Greenwich getaway is found here.

Homestead Inn-Thomas Henkelmann

8.0 Very good (13 reviews)

Kent: Connect with nature


There are a couple of small cultural points of interest in Kent, like the Sloane-Stanley Museum with its 19th century cabin and the ruins of Kent Furnace, but the big reason to visit is nature.

While the Catskills are less than two hours away, Kent Falls State Park has more than enough natural beauty for a Connecticut weekend getaway in the great outdoors. Whether you go for fishing, hiking, or even just a pleasant picnic, you won’t want to miss the covered bridge or the park’s famed waterfalls, cascading about 250 feet to the river below.

There’s also a quaint art trail with some outdoor exhibits worth checking out while you’re here.

If your heart is intent upon enjoying the park (and it should be), be prepared to wait a bit before entering. There’s a 10-space parking lot with no other parking available, and the park is officially closed whenever the spaces are full, so you may need to cool your heels while others are exploring; fortunately, it’s not a heavily populated area. Kent is particularly picturesque in fall, when the vibrant foliage presents a brilliant scene.

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Couples, small families, and best friends will all love The Spirit Horse Farm. This vacation rental offers a richly furnished and decorated barn converted to offer multiple bedrooms and bathrooms to satisfy any modest family or friend group. Entertainment includes a billiards room, ping-pong table, full gym, and plenty of games, but the outdoor spaces are what truly make this property pop. Take an afternoon swim in the in-ground pool and explore the organic gardens by day before ending the evening with drinks by the fire pits. Be sure to say hello to the farm’s peacock, chicken and horse guests when they’re around.

The Spirit Horse Farm In Kent, Ct.

9.4 Excellent (171 reviews)

Hartford: Kick up your heels in the capital


Hartford may not be Connecticut’s largest city, but it is the capital and it’s home to plenty of museums, historic houses, and outdoor activity. Start out by getting a feel for city and state history at the Connecticut Historical Society, where you’ll find seven exhibits (including the permanent exhibit, “Making Connecticut”) at this home of hundreds of historical artifacts spanning all facets of city and state culture.

From here, head to the considerably larger Connecticut Science Center, with six floors hosting more than 150 interactive exhibits that are both educational and entertaining, particularly for the younger members of your group who are welcome to touch.

Finish your museum marathon with the Wadsworth Atheneum Museum of Art, where an enormous collection of primarily European and American art is housed within the castle walls of the country’s oldest, continually-operating art museum.

There are plenty of historic houses in Hartford, but the two you definitely won’t want to miss are Mark Twain House, with architecture and design as fascinating as its famous former inhabitant and the classics he penned here, and Harriet Beecher Stowe Center, leaving no doubt of Hartford’s indelible contribution to great American literature.

Finally, spend some time outdoors, choosing from the romance of Elizabeth Park‘s poetic settings and epic rose garden, the trails of Bushnell Park (the country’s oldest publicly funded park), or Great River Park with riverfront trails dotted by sporadic public art.

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A Connecticut weekend getaway in the city requires both comfort and inspiration for total recharge and rejuvenation throughout, so base yourself at The Goodwin on Haynes Street. This design-forward boutique hotel comes with serious style and true luxury in all of its rooms, but small groups and families should consider its unique duplex suites. These two-story stays offer plenty of space and a true sense of home-away-from-home with all the hotel conveniences and amenities you need on your busy city getaway, and the central downtown location couldn’t be more convenient to whichever Hartford activities you choose to round out your itinerary.

The Goodwin

9.2 Excellent (2012 reviews)