Top Vacation Destinations Within a 3-Hour Drive of Fairfield County


A bed and breakfast at a travel destination.It’s that time of year again when the weather gets cold enough that we all start dreaming of warmer weather and summer vacations! As a mom of two daughters, I can relate to wanting to find a great family getaway that is relatively close to home.

Car trips with little kids can be challenging, and there are many wonderful destinations within three hours of Fairfield County that the whole family can enjoy!

1. Mystic, Connecticut

Nestled along the picturesque coastline, Mystic blends history, charm, and family-friendly attractions. The Mystic Seaport Museum offers an immersive experience, allowing families to explore historic ships, engage in hands-on activities, and witness maritime traditions come to life. The Mystic Aquarium is another gem, captivating visitors with its diverse marine life exhibits and interactive shows.

The quaint downtown area exudes a welcoming atmosphere with boutique shops, delectable seafood restaurants, and vibrant art galleries. Families can enjoy scenic boat rides along the Mystic River or embark on a captivating journey at the Mystic Pizza restaurant, made famous by the film. 

2. Newport, Rhode Island

It is an ideal family vacation destination, seamlessly merging historical charm, coastal beauty, and a plethora of family-friendly activities. The city is renowned for its opulent Gilded Age mansions, which offer fascinating tours and glimpses into America’s past. Families can explore the Newport Cliff Walk, a scenic trail along the coastline providing breathtaking views of the Atlantic Ocean and the magnificent mansions.

The lively Newport Harbor beckons with sailing excursions, harbor tours, and seafood dining options, creating a nautical atmosphere that appeals to all ages. Additionally, the interactive and educational experiences at places like the International Tennis Hall of Fame cater to diverse interests. With its rich history, coastal allure, and family-centric attractions, Newport, RI, stands as an enchanting destination for a memorable family vacation.

3. Mohonk Mountain, New York

It is a splendid location, offering a perfect blend of natural beauty and recreational opportunities. The Mohonk Mountain House provides a unique and idyllic setting for families to unwind and connect with nature. The resort offers various outdoor activities, including hiking, rock climbing, and boating on Lake Mohonk, allowing families to embrace the surrounding landscape.

The Victorian-style Mohonk Mountain House is a destination within a destination, featuring charming accommodations, delicious dining options, and a relaxing spa. In essence, Mohonk Mountain stands as an exceptional family vacation spot, providing an immersive nature experience coupled with the comforts of a resort setting.

4. The Berkshires, Massachusetts

It is an exceptional family vacation location, boasting a blend of cultural richness and natural beauty. Families can immerse themselves in the vibrant arts scene with visits to institutions like Tanglewood, the summer home of the Boston Symphony Orchestra, or the Norman Rockwell Museum. The region offers abundant outdoor activities, from hiking scenic trails in the Appalachian Mountains to enjoying water-based fun at picturesque lakes like Pontoosuc and Onota.

Charming towns such as Lenox and Stockbridge provide a welcoming atmosphere with quaint shops, local eateries, and cultural events. Whether exploring the Berkshire Botanical Garden, attending family-friendly performances at local theaters, or simply enjoying the breathtaking landscapes, the Berkshires offer a diverse and enriching experience that makes it an ideal family vacation destination.

5. Saratoga Springs, New York

Blending historical charm with a vibrant atmosphere and a range of family-friendly activities. Famous for its mineral springs, Saratoga Spa State Park offers a unique experience with its rejuvenating baths and relaxing ambiance. Families can enjoy the thrill of horse racing at the historic Saratoga Race Course, adding an exciting and timeless element to their visit.

The city’s downtown area has charming boutiques, delicious eateries, and cultural attractions like the Saratoga Performing Arts Center. Families can explore the Children’s Museum at Saratoga, offering interactive exhibits for the younger ones, or stroll through Congress Park with its charming carousel and tranquil gardens. With its diverse offerings, from outdoor recreation to cultural exploration, Saratoga provides a perfect blend for a memorable and enjoyable family vacation.

6. The Pocono Mountains, Pennsylvania

A diverse range of activities amidst stunning natural surroundings. Known for its scenic beauty, the region provides ample opportunities for outdoor adventures, including hiking, biking, and water activities in the pristine lakes. The Poconos cater to families with various interests, featuring family-friendly resorts with amenities like water parks, mini-golf, and organized activities for children.

The area transforms into a snowy wonderland in the winter, with opportunities for skiing, snowboarding, and other winter sports. Charming towns like Jim Thorpe and Stroudsburg add a cultural touch with their boutiques, galleries, and local cuisine. Whether seeking relaxation in nature, enjoying thrilling adventures, or exploring cultural gems, the Pocono Mountains offer a well-rounded and memorable family vacation experience.

7. Watch Hill, Rhode Island

An enchanting family vacation destination, captivating visitors with its coastal charm and family-friendly offerings. Nestled along the pristine shoreline, Watch Hill has beautiful sandy beaches where families can soak up the sun, build sandcastles, and enjoy the refreshing Atlantic Ocean. The iconic Watch Hill Lighthouse adds a touch of maritime history to the scenery.

The area is home to the Watch Hill Carousel, a vintage ride that delights children and adults alike. Families can explore the quaint village with boutique shops, ice cream parlors, and seafood restaurants. The nearby Napatree Point Conservation Area provides nature walks and bird-watching opportunities. With its picturesque landscapes, charming community, and a perfect mix of relaxation and recreation, Watch Hill creates a delightful setting for a memorable family vacation.

8. Southern Vermont

This area blends scenic beauty, outdoor recreation, and charming communities. The region’s picturesque landscapes offer a haven for outdoor enthusiasts with opportunities for hiking, skiing, and exploring nature trails. Families can experience the magic of winter sports at renowned ski resorts like Stratton and Mount Snow, transforming the area into a snowy playground.

Quaint villages such as Manchester and Wilmington provide a blend of historic charm and modern amenities, featuring local shops, galleries, and delicious dining options. Southern Vermont’s family-friendly atmosphere extends to activities like horseback riding, farm visits, and seasonal festivals, ensuring there’s something for everyone. Whether enjoying the vibrant fall foliage or partaking in winter adventures, Southern Vermont creates lasting memories for families seeking a peaceful retreat with a touch of New England charm.

These destinations offer a little something for everyone, whether your vibe is a beach vacation or a hike in the mountains. Your next escape can be just a short drive away, especially if you aim to go away for a weekend! 

Kate Aufiero is a travel advisor and a Wilton mom of two. She works with individuals and families to plan comprehensive vacations that the whole family will enjoy. To contact Kate, please email her at [email protected] and follow along with her tips and travel on Instagram.  


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