Weekend Getaways In CT: Top 21 Most Unique Spots (+Map) | Stanton House Inn

Sunset along the waterfront, close to the Seven Sisters Hills

Looking for a unique weekend getaway? Connecticut’s got it all! Nestled between:

  • Rhode Island
  • Massachusetts
  • New York State
  • And Long Island Sound

This little gem of a state offers adventures galore. From charming towns and lively cities to breathtaking landscapes, the Nutmeg State is the perfect spot for a quick getaway.

Picture this: strolling along pristine beaches, hiking lush trails, or exploring a nature reserve. Maybe you’re more into quaint villages where time stands still. But hold on, Connecticut’s not just about nature. Art lovers, history buffs, and science nerds will find top-notch museums. Foodies can dig into fantastic restaurants. And if you love the sea, there are plenty of seaside spots to explore!

And guess what? You can stay in anything from luxury hotels and cozy inns to unique treehouses. Yep, treehouses!

So, whether it’s a romantic getaway or a quick city break, Connecticut is where it’s at. It’s more than a state; it’s a state of mind. So why wait? Pack your bags and dive into the beauty of Connecticut. Your unique weekend adventure awaits!

Ready to explore the best weekend getaways in Connecticut? Let’s get into it:

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 soak in 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 CT

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

Get ready to explore the best weekend spots Connecticut has to offer! From Mystic’s maritime wonders to Simsbury’s rich history, from Greenwich’s high-end lifestyle to New Haven’s vibrant culture, there’s something for everyone.

Whether you’re after a romantic getaway or a family adventure, these top 10 Connecticut destinations promise unforgettable experiences.

1) Mystic

Ah, Mystic, CT! This coastal harbor town is perfect for maritime lovers. Check out the Mystic Aquarium and the Mystic Seaport Museum. And who can forget Mystic Pizza, from the 1988 movie?

Stroll through downtown Mystic for fine dining and cute shops. Boutique hotels like the Whaler’s Inn offer a cozy vibe for romantic getaways. You’ll fall in love with this charming town.

2) Old Saybrook

Lighthouse in Old Saybrook, Connecticut

Old Saybrook is New England charm at its best. This historic town features sites like the General William Hart House and stunning beaches. Lose yourself in the beauty of the Connecticut River, explore hiking trails, or relax by the pool at Saybrook Point Resort. For one of the most perfect summer weekend getaways in New England, the town of Old Saybrook, CT, is the place to be.

3) Stonington

Stonington, sitting pretty by the Long Island Sound, Fishers Island Sound, and the Mystic River, is the perfect coastal escape. Stroll through downtown Stonington, CT, where art galleries, antique shops, and seafood restaurants line the streets. If you’re into nature, don’t miss Rocky Neck State Park for a refreshing outdoor summer weekend getaway.

Soak in the stunning coastal views and let the salty breeze whisk your worries away at this historic small town. If you need more adventure, Rhode Island and Block Island are just a short drive away.

4) Simsbury

Nestled in the Farmington River Valley, Simsbury is a charming New England town with a rich history and beautiful landscapes. It’s a playground for outdoor lovers.

Explore Simsbury, Connecticut to enjoy these attractions:

The views from Heublein Tower will leave you speechless, especially during fall foliage season. Simsbury and nearby Avon, CT, is the perfect blend of nature and history.

5) Madison

Water views at Hammonasset State Park in Madison, CT, near the Madison Beach Hotel

Madison, CT, a dreamy coastal town, offers:

  • Gorgeous beaches for summer fun
  • Unique bookstores
  • Cozy cafes
  • Nature trails and walking trails like the Shoreline Greenway Trail
  • A great spa, at Sea Spa

Stay at the luxurious Madison Beach Hotel (or just use the spa) and explore nearby attractions like Meigs Point Nature Center at Hammonasset Beach State Park. This quaint town is perfect for a romantic weekend getaway.

6) Greenwich

Greenwich blends luxury with culture, and only an hour north of NYC, with traffic. Choose from swanky hotels to cozy B&Bs. Greenwich Avenue offers fine dining and shopping galore. And the town is rich in cultural spots like museums, galleries, and theaters, too.

Treat yourself to a charming weekend in Greenwich, Connecticut, and unwind at the elegant Stanton House Inn, oozing Old World charm. Our outdoor pool and continental breakfast makes us quite popular for summer getaways in Connecticut.

7) New Haven

New Haven is a lively hub of arts, culture, and history. Home to Yale University, it offers diverse dining options and historic sites.

Discover Yale’s treasures! Visit the Art Gallery, explore the Beinecke Rare Book & Manuscript Library, and dive into the Yale British Art Center. Or try your hand at the largest indoor ropes course at the local Jordan’s furniture store. With so much to see and do, New Haven is the ideal weekend getaway for an urban adventure.

8) Hartford

Hartford, Connecticut’s capital, is a treasure trove of adventure and beauty. Here’s a quick guide to 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
  • Stroll through the Connecticut State Capitol
  • Catch a game at Dunkin’ Donuts Park

Don’t miss the Connecticut Science Center or the stunning Elizabeth Park Rose Gardens. Hartford is the perfect spot for a fun-filled weekend getaway in Hartford!

9) Litchfield

Litchfield, a charming historic town in Litchfield County, is like stepping back in time. Wander through the Litchfield Historic District to see beautifully preserved homes, lush gardens, and the picturesque Litchfield Hills.

This town’s rich history and breathtaking scenery make it a peaceful escape from daily life. The local Litchfield Inn is a cozy place to stay while you explore. And the White Memorial Conservation Center is a personal favorite among hiking trails in the area.

10) West Hartford

West Hartford perfectly blends city sophistication with small-town charm. It boasts a diverse dining scene, trendy shopping, and cultural attractions like the Elizabeth Park Rose Garden. Ideal for a weekend getaway, West Hartford promises excitement and new experiences. Plus, it’s cool 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

Looking for a dash more charm in your weekend escape? These five towns are perfect for romantic getaways, each offering a unique blend of history, culture, and stunning landscapes.


Essex is a delightful town with rich history and stunning scenery. Hop aboard the historic Essex Steam Train & Riverboat and enjoy tales of the area’s past while soaking in scenic views.

Explore the downtown area of Essex, home to unique shops and eateries. The famous Essex Steam Train and Riverboat are must-sees!


Nestled in Connecticut’s Litchfield Hills, town of Kent is a hidden gem. With stunning vistas, vintage buildings, and plenty of outdoor activities, it’s perfect for a weekend escape. Check out:

  • The Appalachian Trail
  • Kent Falls Trail
  • And Macedonia Brook State Park

Or schedule a tour with the local Bicycle Tour Company, if you want to be gentler to your knees.

Local shops offer unique finds, and Kent’s culinary delights are a treat. Don’t miss Kent Falls State Park during your visit!


Nestled in the Connecticut River Valley, Chester is a charming riverside town perfect for a relaxing weekend getaway. Here’s what you can do in Chester:

  • Check out the cozy cafes and gift shops
  • Take a ferry ride to Gillette Castle State Park
  • Catch a show at the Norma Terris Theatre
  • Sip some craft beer at Little House Brewing Co., one of the best breweries in Connecticut

Chester offers a peaceful escape, ideal for unwinding and reconnecting with nature.


Resting on the shores of Long Island Sound, village of Niantic, Connecticut is a coastal haven perfect for a weekend retreat. With beautiful beaches, unique shops, and delicious eateries, Niantic is 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 river views, and explore the lovely beaches, parks, and cafes. The beaches here, Walnut Beach and Silver Sands State Park, are fantastic for beach getaways in Connecticut.

With its scenic river, sun-soaked beaches, and historic architecture, Milford is perfect for a romantic weekend.

A few more ideas for weekend trips in CT

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

Still hungry for more Connecticut weekend trip ideas? Then read on!

From luxurious resorts and casinos to charming small towns and picturesque landscapes, these Connecticut weekend getaway destinations offer 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 is a unique small town that blends urban elements with picturesque scenery. Enjoy 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 a show at the Westport Country Playhouse to add a touch of culture to your weekend.


Uncasville is home to the Mohegan Sun Casino & Resort, a destination offering:

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


Cornwall has an enchanting small town vibe with historic buildings, a scenic covered bridge, and nearby forest trails. Discover the West Cornwall Covered Bridge or explore the Mohawk Mountain Ski Area and Mohawk State Park and Forest.

Cornwall offers a peaceful weekend getaway, perfect for escaping the hustle and bustle of city life.

New Canaan

The Philip Johnson glass house

New Canaan is a blend of history, culture, and outdoor fun, perfect for a weekend escape. Don’t miss:

Dive into the beauty and charm of New Canaan. With so many things to see and do, New Canaan, Connecticut, it’s an ideal spot for a weekend getaway.


Woodstock, CT, is a charming town full of beautiful landscapes, quaint shops, and outdoor adventures. Check out:

  • Woodstock Valley Country Store
  • Roseland Cottage
  • Taylor Brooke Winery
  • Scranton’s Shops

Woodstock offers a peaceful escape, perfect for reconnecting with nature.


A picture of a historic building in Connecticut, perfect for a weekend getaway to get some fresh air

Home to the Water’s Edge Resort and Spa, Westbrook features:

  • A private beach
  • A spa
  • Various dining options
  • Nearby attractions

Relax on the shores of Long Island Sound or visit nearby spots like the Yale University Summer Music Festival, Music Mountain, and College Street Music Hall. Westbrook is perfect for a tranquil weekend of relaxation and rejuvenation.


Connecticut is a treasure trove of weekend getaways, from charming small towns to vibrant cities and picturesque landscapes. Whether you want adventure, relaxation, or romantic getaways, Connecticut has something for everyone. So pack your bags, hit the road, and discover the enchanting destinations in the beautiful Nutmeg State.

Frequently Asked Questions

How do I plan a mini road trip?

To plan a mini road trip:

  • Get a vehicle check-up
  • Choose a destination and route
  • Make an itinerary
  • Budget
  • Book accommodations
  • Bring a real map
  • Pack light
  • Allow for spontaneity
  • Take plenty of breaks

What is the best travel day driving?

For a smooth and safe journey, Sunday is best for long-distance driving due to less traffic. Tuesdays have the fewest crashes, according to the NHTSA.

How to do a 12 hour road trip?

A 12-hour road trip can be great with the right prep:

  • Get plenty of sleep beforehand
  • Bring healthy snacks and water
  • Plan rest stops
  • Chew gum
  • Use energizing scents
  • Keep passengers entertained
  • Take turns driving if possible

Are there any luxurious resorts and spas in Connecticut?

Yes! Indulge at Saybrook Point Inn & Spa, Water’s Edge Resort and Spa, or the award-winning boutique hotel Mayflower Inn & Spa in Washington, Connecticut.

Updated and republished: June 24, 2024

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