Craving a sophisticated getaway that still feels small-town cozy? I always recommend Ridgefield, Connecticut. Nestled at the edge of the Berkshire Mountains, this gem has become one of my favorite escapes. You’ll find just the right mix of colonial charm and cultural depth. Whether I’m wandering Main Street or catching a performance in town, Ridgefield always helps me slow down and recharge—without straying too far from New York City.
Ridgefield, CT Highlights I Think You’ll Love:
- For Families: Visit the Aldrich Contemporary Art Museum – I’ve visited with friends and their kids, and we all enjoyed the modern art exhibits. You’ll find it thoughtful, creative, and welcoming to all ages.
- For Outdoor Enthusiasts: Hike at Bennett’s Pond State Park – If you’re anything like me, you’ll appreciate these serene, wooded trails. I’ve spotted herons, taken photos by the pond, and left feeling completely refreshed.
- For Kids: Play and picnic at Ballard Park – You’ll want to bring a blanket. I’ve picnicked under the trees, listened to live music, and watched little ones run around the gardens and playgrounds.
- For an Adventure: Explore Pine Mountain Reserve – I hiked this on a cool autumn morning and the views were spectacular. If you enjoy a challenge, you’ll love it too—especially with a camera in hand.
- For Shoppers: Browse boutiques along Main Street – I can never resist Ridgefield’s charming downtown. You’ll find handcrafted goods, curated home décor, and cafés that make it easy to linger longer.
Best Time to Visit Ridgefield, CT
If I had to choose, I’d say spring and fall are unbeatable. I’ve visited during both seasons and the scenery truly takes your breath away—blooms in spring, fiery foliage in fall. You’ll also love summer if you enjoy outdoor concerts (I always pack a lawn chair), while winter brings a cozy, festive vibe with live performances and holiday sparkle.
How to Get to Ridgefield, CT
- By Car: I usually drive in via Route 7 or Route 35—it’s just 90 minutes from New York City and under an hour from New Haven, making it a perfect weekend trip.
- By Train: I’ve taken the Metro-North to Katonah before, then grabbed a quick rideshare into Ridgefield. If you don’t mind the last short leg by car, it’s a smooth and scenic route.
- By Air: I’ve flown into Westchester County Airport—it’s only 35 minutes away. You could also fly into Bradley or NYC airports if you’re coming from farther out.
Where I Like to Stay in Ridgefield, CT
- West Lane Inn – This historic inn is a personal favorite. You’ll enjoy its elegant charm and walkable access to shops and restaurants—it feels like a home away from home.
- Fife ‘n Drum Inn (Kent) – If you want a rustic countryside feel, I’ve stayed here and loved the fine dining and sweeping mountain views. It’s about 45 minutes away, but worth the drive.
- Vacation Rentals – I’ve booked cozy cottages and farmhouse retreats here for longer stays. You’ll find lovely homes perfect for family trips or romantic weekends for two.
Best Things to Do in Ridgefield, CT
Prospector Theater - Catch a movie and support a mission-driven venue on an affordable family outing.
Aldrich Contemporary Art Museum - Explore bold exhibits and admire modern creativity on an unusual cultural trip.
Keeler Tavern Museum and History Center - Tour historic rooms and discover colonial stories on an educational weekend visit.
ACT of Connecticut - Enjoy Broadway-caliber shows and support local talent on an exciting night out.
Ridgefield Theater Barn - Laugh at comedies and see community plays on a fun cheap trip.
Seth Low Pierrepont State Park - Hike wooded trails and paddle the lake on a peaceful retirement escape.
Bennett's Pond State Park - Explore quiet paths and look at scenic views on an easy spring trip.
Weir Farm National Historic Site - Admire artist studios and walk through inspiring landscapes on a romantic couples outing.
In Summary...
(and if you want to revisit my photo journey)