Feel Farther Away in Fairfield County

This itinerary is all about packing in the fun within a tight radius. Charming towns, local eats, and hidden gems are all nearby — so you can do more and stress less. Pick your favorites, plan your days your way, and leave room for unforgettable detours. You can even view all the spots on the map at the bottom!

Craving a quick escape from the everyday? Fairfield County delivers the perfect 2–4 day getaway that feels worlds away — without going far from home. Picture it: stunning waterfront views, unmatched shopping, foodie finds, arts and culture hits, and natural beauty that thrills and chills. All within 25 miles.

2-4 days

  • Spring
  • Summer
  • Fall

  • Stay Overnight
  • Hang at the Beach
  • Visit Modern & Historic Homes
  • Shop Famous Streets
  • Sip Beer (Alcoholic and Non-alcoholic)
  • See a Show
  • Dine with Flavor
  • Make Animal Friends
  • Soak Up Unique Cities
  • Take a Hike
  • Find Nightlife

Visit Modern & Historic Homes

Looking to immerse yourself in culture? Try visiting The Glass House for a modern marvel built by architect Philip Johnson. The house sits on a stunning 49-acre landscape. Or step back in time at the Lockwood-Mathews Mansion, an award-winning historic site built between 1864 and 1868. Designed by architect Detlef Lienau, the mansion was commissioned by financier and railroad baron LeGrand Lockwood and his wife, Ann Louisa. Plus, find even more history at the spots below.

* Editor's Picks

Shop Famous Streets

When in Fairfield County, you simply must go shopping. Explore the renowned Greenwich Avenue for upscale stores, stroll downtown Westport for your favorite brands, and head to downtown New Canaan for small-town charm, boutiques, and cafes. Each spot offers well-known, top tier shopping.

Sip Beer (Alcoholic and Non-alcoholic)

Got a taste for craft beer? There's a lot to love in Fairfield County, where you'll find a great mix of beer gardens, breweries, and even nationally-recognized non-alcoholic beer at Athletic Brewing Company. Discover the suggestions below for a variety of options!

* Editor's Picks

See a Show

While you're in town, catch a show at the legendary Westport Country Playhouse — founded by iconic Hollywood couple Paul Newman and Joanne Woodward, who shared both a deep love for the arts and a rare, lifelong partnership. Paul, a longtime Westport resident, passed away years ago, but Joanne remains connected to the theater’s legacy today. Plus, check out all the creative hubs for theater nearby, many listed below.

* Editor's Picks

Dine with Flavor

Foodies will love Fairfield County, home to a wide array of top-tier restaurants. Savor meals by James Beard nominees at The Cottage. Or find incredibly over-the-top, Insta-worthy brunch at Elm Street Diner. From award-winning restaurants like Bar Rosina and Elm, to seafood, barbcue, and more, there are so many ways to eat well. Find some great ideas below.

* Editor's Picks

Make Animal Friends

Take a walk on the wild side! Take the kids to see creatures from tigers to otters, giant octopus, and more at Fairfield County's lively animal attractions below. Looking for more? Find even more to do with the kiddos here.

* Editor's Picks

Soak Up Unique Cities

Want to escape the hustle, but keep the fun city vibes? Stamford and Norwalk strike the perfect balance: easy access to nature with nightlife, dining, and downtown energy just moments away.

Norwalk, nicknamed “Oyster Town,” boasts the most shoreline of any Connecticut city and a rich maritime history — making it a top spot for seafood lovers and waterfront views. Stamford is home to the stunning Bartlett Arboretum & Gardens, with 93 acres of trails, parkland, and blooms — a serene escape right in the city.

Want to learn tips from the locals? Check out these ideas for enjoying the cities of Stamford and Norwalk.

Find Nightlife

Ready to go out? Head to SoNo (South Norwalk) for great bars and late night vibes. Plus, check out the spots below. 

* Editor's Picks

Map