Weekend Getaways In CT: Top 21 Most Unique Spots | Stanton House Inn

Sunset along the waterfront, close to the Seven Sisters Hills

Looking for a unique weekend getaway? Connecticut has got you covered! Nestled between Rhode Island, Massachusetts, New York, and the Long Island Sound, this gem of a state offers a smorgasbord of adventures. From charming towns and bustling cities to scenic landscapes, the Nutmeg State is your stage for weekend getaways in CT.


Imagine this: you’re strolling along pristine beaches or exploring lush hiking trails. Maybe you’re getting lost in a nature reserve. You might prefer a visit to a quaint village where time seems to have stood still. But Connecticut offers more than just that. For the culture vultures, it boasts top-notch art, history, and science museums. The foodies can enjoy a plethora of excellent restaurants. And for lovers of the sea, there are plenty of seaside attractions to explore!


But wait, there’s more! You can choose from a variety of accommodations, ranging from luxury hotels and cozy inns to unique treehouses. Yes, you heard it right, treehouses!


So whether you’re planning romantic weekend getaways or a quick city break, Connecticut is the place to be. It’s not just a state, it’s a state of mind. So why wait? Pack your bags and get ready to explore the beautiful landscape that is Connecticut. Your unique weekend getaway awaits!


Quick hits:

  • Escape the routine and explore CT’s unique weekend getaways, from Mystic to New Canaan!
  • Experience small town charm in Essex, Kent, Chester & Milford.
  • Take a gamble at Mohegan Sun or explore Westport’s city vibes for an unforgettable adventure!


Map of the best weekend getaways in CT
Map design by Stanton House Inn


Top 10 Weekend Getaways in Connecticut

A picture of a beautiful beach in Connecticut, perfect for a weekend getaway

Get ready to journey through the best weekend getaways Connecticut has to offer! From Mystic’s maritime wonders to Simsbury’s deep-rooted history, from the high-end lifestyle of Greenwich to New Haven’s vibrant cultural scene, there is a destination for every type of traveler.


Whether you’re seeking romantic getaways or a family-oriented adventure, these top 10 destinations in Connecticut promise to deliver unforgettable experiences.

1) Mystic

Ah, Mystic, CT! This delightful coastal town is a top choice for those drawn to maritime adventures. With attractions like the Mystic Aquarium and the Mystic Seaport Museum, there’s no shortage of excitement. And who could forget the famous Mystic Pizza, featured in the eponymous 1988 movie?


Stroll through downtown Mystic, which offers fine dining and cute shops. The boutique hotels, especially the Whaler’s Inn, boast an atmosphere ideal for romantic getaways. You’ll be swept away by the charm of this coastal town.


2) Old Saybrook

Lighthouse in Old Saybrook, Connecticut

Old Saybrook embodies the quintessential charm of New England. The town of Old Saybrook, CT, is a historic small town that captivates with its sites like the General William Hart House and stunning beaches. It’s the perfect place to lose yourself in the beauty of the Connecticut River. You can explore nearby hiking trails or relax by the outdoor pool at the luxurious Saybrook Point Resort. For a breath of fresh air, Old Saybrook offers one of the most ideal summer weekend getaways in New England.


3) Stonington

Stonington, resting along the Long Island Sound and the Mystic River, is a captivating coastal town ideal for a weekend escape. Take a leisurely stroll through the streets of downtown Stonington, CT. Art galleries, antique stores, and restaurants serving mouthwatering seafood line the charming streets. Don’t miss the opportunity to visit the nearby Rocky Neck State Park for a refreshing outdoor experience.


Take a moment to soak in the breathtaking coastal views and let the salty breeze carry your worries away. And if this harbor town isn’t enough, drive a short way over to Rhode Island for even more things to do, Block Island.


4) Simsbury

Located in the Farmington River Valley of Hartford County, Connecticut, Simsbury is an enchanting hamlet. Renowned for its illustrious past and picturesque landscapes, Simsbury is a small town full of New England charm. It offers an abundance of outdoor activities for visitors to enjoy.


Explore Simsbury, Connecticut to enjoy these attractions:


The views of the Farmington River Valley from the Heublein Tower across Simsbury and the town of Avon, CT, will leave you speechless. And that goes double during fall foliage season. Simsbury is the perfect getaway to immerse yourself in nature and history.

5) Madison

Water views from Madison, CT, near the Madison Beach Hotel

Madison, a dreamy coastal town on the CT shoreline, boasts:

  • Stunning beaches, perfect for summer getaways
  • Exceptional bookstores
  • Cozy cafes
  • A wealth of activities immersed in nature, including the Shoreline Greenway Trail


Relax at the Madison Beach Hotel, a luxurious retreat. While you’re here, be sure to explore the nearby attractions such as the Meigs Point Nature Center in Hammonasset Beach State Park.


This charming old-fashioned town offers the perfect setting for a romantic weekend getaway.

6) Greenwich

Enter Greenwich, a harmonious blend of luxury and culture! This upscale town offers an array of lodging options, from swanky hotels to a cozy bed and breakfast with continental breakfast. Greenwich Avenue offers a diverse selection of restaurants for you to indulge in. It’s also home to a ton of cultural attractions, including museums, galleries, and theaters.


Unwind and treat yourself to a charmingly elegant weekend in Greenwich, Connecticut, at Stanton House Inn.

7) New Haven

New Haven thrives as a vibrant center for arts, culture, and history. Home to Yale University, this vibrant city offers a diverse range of dining options and historic sites.


Unearth the treasures at Yale University! Visit the Art Gallery, explore the Beinecke Rare Book & Manuscript Library, and immerse yourself in the Yale Center for British Art. With so much to see and do, New Haven is the ideal Connecticut weekend getaway for those seeking a dynamic urban experience.

8) Hartford

Hartford, the capital of Connecticut, is an enticing city filled with both adventure and beauty. Here are some of the best things you can do in Hartford, CT:

  • Explore the Mark Twain House & Museum
  • Visit the Wadsworth Atheneum Museum of Art
  • Enjoy a show at Hartford Stage
  • Take a stroll through the Connecticut State Capitol
  • Catch a game at Dunkin’ Donuts Park


The Connecticut Science Center and Elizabeth Park Rose Gardens are just a few of the many attractions available in this vibrant city. Experience the perfect weekend getaway in Hartford!

9) Litchfield

Litchfield, a quaint historic town nestled within Litchfield County, Connecticut, invites you to step back in time. Take a leisurely walk through the Litchfield Historic District, where you can marvel at well-preserved homes, lush gardens, and the awe-inspiring views of the Litchfield Hills.


With its rich history and breathtaking scenery, Litchfield offers a tranquil escape from the hustle and bustle of daily life. And the local Litchfield Inn is an ideal pied-à-terre while you’re there.

10) West Hartford

West Hartford, a town that perfectly balances city sophistication with small-town charm, is worth exploring. It boasts a diverse dining scene and trendy shopping. The town also offers cultural attractions like the Elizabeth Park Rose Garden. Ideal for a Connecticut weekend getaway, West Hartford promises both excitement and new experiences. And the town is hip enough to host a boutique hotel or two.

The 5 Cutest Towns for Connecticut Weekend Getaways

A picture of a small town in Connecticut, perfect for a weekend getaway

Seeking a dash more charm in your weekend escape? These five cutest towns for romantic getaways are just the ticket! These towns, brimming with character and scenic beauty, provide an ideal setting for a memorable escape. Each town offers a unique blend of history, culture, and stunning landscapes.



Essex, a delightful town, captivates with its rich history and stunning scenery. Hop aboard the historic Essex Steam Train & Riverboat and let the conductor regale you with tales of the area’s past while you take in the scenic views.


Be sure to explor the downtown area of Essex, where the famous Essex Steam Train and Riverboat is located. The area is also home to a variety of unique shops and eateries.



Tucked away in Connecticut’s Litchfield Hills, the town of Kent is a hidden treasure. Its stunning vistas, vintage buildings, and an array of outdoor activities make it a picturesque destination for a weekend escape. Take time to explore the Appalachian Trail, Kent Falls Trail, and Macedonia Brook State Park. The local shops offer unique finds and the culinary delights of Kent are worth indulging in. A visit to the breathtaking Kent Falls State Park is a must during your stay.


Situated in the Connecticut River Valley, Chester is a delightful riverside town that promises a relaxing weekend getaway. Here are some things you can do in Chester:

  • Visit the cafes and gift shops
  • Take a ferry ride to Gillette Castle State Park
  • Enjoy a show at the Norma Terris Theatre
  • Discover the Little House Brewing Co., one of the best breweries in Connecticut


Chester offers a tranquil escape perfect for unwinding and reconnecting with nature at the White Memorial Conservation Center.


Resting on the shores of the Long Island Sound, the village of Niantic, Connecticut, is a coastal haven ideal for a weekend retreat. Boasting beautiful beaches, unique shops, and mouthwatering eateries, Niantic offers an idyllic escape.


Stay at the waterfront Inn at Harbor Hill Marina and explore nearby attractions like the Niantic Bay Boardwalk, Niantic Children’s Museum, and Hole-in-the-Wall Beach.


Milford, CT, is a quaint old-fashioned town on the Connecticut coast, offering an English-inspired atmosphere. Wander the charming streets, take in the stunning views of the river, and explore the beautiful beaches, parks, and cafes. The beaches here, Walnut Beach and Silver Sands State Park, are fantastic beach getaways in Connecticut.


With its charming river, sun-soaked beaches, and historic architecture, Milford is the perfect destination for a romantic weekend getaway.

A few more ideas for weekend trips in CT

A picture of a scenic landscape in Connecticut, perfect for a weekend getaway

If your desire for Connecticut weekend trip ideas remains unsatiated, your search ends here!


From luxurious resorts and casinos to charming small towns and picturesque landscapes, these destinations offer their own unique attractions, activities, and things to do in Connecticut.


So pack your bags and set off on an unforgettable Connecticut adventure.


A scenic view of Westport, Connecticut, a perfect destination for weekend trips from CT

Westport, a distinct small town, presents a blend of urban elements and picturesque scenery. Indulge in a variety of dining options, shop at trendy stores, and relax on beautiful beaches like Compo Beach, Sherwood Island State Park, and Burying Hill Beach.


Don’t miss the chance to catch a show at the Westport Country Playhouse, adding a touch of culture to your weekend getaway.



Uncasville hosts the Mohegan Sun Casino & Resort, a comprehensive destination offering:


There’s something for everyone at this exciting boutique hotel resort. Treat yourself to a weekend of indulgence and excitement in Uncasville.


Cornwall, an enchanting small town, is replete with historic buildings, a scenic covered bridge, and forest trails in close proximity. Discover the West Cornwall Covered Bridge or explore the nearby Mohawk Mountain Ski Area and State Forest.


Cornwall offers a peaceful weekend getaway for those seeking a break from the hustle and bustle of city life.

New Canaan

The town of New Canaan provides an impeccable mix of history, culture, and outdoor pursuits for an ideal weekend escape. Some must-visit attractions include:


Immerse yourself in the beauty and charm of New Canaan. With so many things to see and do, New Canaan, Connecticut, is another ideal destination for weekend getaways in Connecticut.


Woodstock, CT, a charming town, is abundant with beautiful landscapes, quaint shops, and outdoor adventures. Visit the Woodstock Valley Country Store, Roseland Cottage, Taylor Brooke Winery, or Scranton’s Shops for a taste of local charm.


With its picturesque landscapes and small-town vibe, Woodstock offers a peaceful escape perfect for reconnecting with nature.


A picture of a historic building in Connecticut, perfect for a weekend getaway

Housing the Water’s Edge Resort and Spa, Westbrook boasts:

  • A private beach
  • A spa
  • Various dining options
  • Attractions in close vicinity


Relax on the shores of the Long Island Sound or take in the sights at nearby attractions like the Yale University Summer Music Festival, Music Mountain, and College Street Music Hall.


Westbrook offers a tranquil weekend getaway perfect for relaxation and rejuvenation.


In summary, Connecticut offers a treasure trove of unique weekend getaways, from charming small towns to vibrant cities and picturesque landscapes. Whether you’re seeking adventure, relaxation, or a romantic escape, Connecticut has something for everyone. So pack your bags, hit the road, and discover the enchanting destinations that await you in the beautiful Nutmeg State.

Frequently Asked Questions

How do I plan a mini road trip?

Planning a mini road trip should include getting a vehicle check-up, deciding on a destination and route, making an itinerary, budgeting, booking accommodations, bringing a real map, packing light, allowing for spontaneity, and taking plenty of breaks.

What is the best travel day driving?

For a smooth and safe journey, Sunday is the best day for long distance driving due to less traffic on the roads, while Tuesdays have the least number of crashes as reported by the NHTSA.

How to do a 12 hour road trip?

A 12 hour road trip can be a great way to get to your destination, but it requires being prepared. Make sure to get plenty of sleep beforehand and bring healthy snacks and plenty of water for during the drive. Also plan rest stops, chew gum, use energizing scents, keep passengers entertained, and take turns driving if possible. Doing all this will make your trip enjoyable and safe.

Are there any luxurious resorts and spas in Connecticut?

Yes, you can indulge in luxury in Connecticut at Saybrook Point Inn & Spa and Water’s Edge Resort and Spa. Or head to Washington, Connecticut, for the award-winning Mayflower Inn & Spa.


Update & republished: April 11, 2024

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