Looking for a sophisticated yet small-town getaway in Fairfield County? Head to Ridgefield! Nestled in the foothills of the Berkshire Mountains, Ridgefield blends colonial charm with cultural vibrancy. Whether you’re strolling Main Street, enjoying a show, or hiking scenic trails, Ridgefield is a peaceful, upscale retreat just a short trip from New York City.

Ridgefield, CT Highlights:

  • For Families: Visit the Aldrich Contemporary Art Museum – A nationally recognized, family-friendly art space focused on thought-provoking modern works.
  • For Outdoor Enthusiasts: Hike at the Bennett’s Pond State Park – Peaceful wooded trails and pond views ideal for hiking, birdwatching, and nature walks.
  • For Kids: Play and picnic at Ballard Park – This beautifully landscaped park has playgrounds, gardens, a gazebo, and seasonal outdoor concerts.
  • For an Adventure: Explore Pine Mountain Reserve – A more challenging hike with panoramic views, perfect for seasoned hikers and photographers.
  • For Shoppers: Browse boutiques along Main Street – A charming, walkable downtown lined with independent shops, art galleries, and cafés.

Best Time to Visit Ridgefield, CT

The best time to visit Ridgefield is in spring and fall, when the town’s gardens bloom or the foliage explodes in vibrant colors. Summer is great for outdoor concerts and events, while winter brings cozy holiday charm and cultural performances at local venues.

How to Get to Ridgefield, CT

  • By Car: Ridgefield is located off Route 7 and Route 35, about 1.5 hours from New York City and 1 hour from New Haven.
  • By Train: Take the Metro-North Harlem Line to Katonah or Branchville, then a short taxi or rideshare into Ridgefield.
  • By Air: The nearest airports are Westchester County Airport (35 minutes), Bradley International Airport, and NYC airports.

Where to Stay in Ridgefield, CT

  • West Lane Inn – A charming historic inn with boutique rooms and a central location near downtown shops and restaurants.
  • Fife ‘n Drum Inn (Kent) – For a nearby rustic escape with fine dining and mountain views, about 45 minutes from Ridgefield.
  • Vacation Rentals – Choose from stylish cottages and countryside homes ideal for family stays or romantic weekends.

Best Things to Do in Ridgefield, CT

Prospector Theater


Catch a movie and support a mission-driven venue on an affordable family outing.

Prospector Theater

© Prospector Theater

The Prospector Theater is a four-screen, first-run movie theater that presents current films from dramas to action and comedy and features a concession stand. The theater is dedicated to employing people with disabilities, using education, engagement, and employment to showcase an individual’s incredible talents. The 26,000 square foot building features four theaters with wheel-chair accessible stadium-style seating, state-of-the-art Christie projectors, Dolby digital surround sound, and Dolby 3D. Ushers meet-and-greet before each show and narrative headsets and closed caption glasses are offered with every first-run feature.

25 Prospect St, Ridgefield, CT 06877, Phone: 203-438-0136

Aldrich Contemporary Art Museum


Explore bold exhibits and admire modern creativity on an unusual cultural trip.

Aldrich Contemporary Art Museum

© Nattapol_Sritongcom/stock.adobe.com

The Aldrich Contemporary Art Museum is a non-collecting contemporary art museum dedicated solely to the exhibition of contemporary art. Founded in 1964 by Larry Aldrich with the aim of becoming one of the first contemporary art museums in the country, the museum is based in an 18th-century former church and general store known as "Old Hundred" which Aldrich bought and converted it into the Larry Aldrich Museum. The Aldrich Museum features works by national and international emerging and mid-career artists, including Jasper Johns, Frank Stella, Robert Rauschenberg, and Cy Twombly. The Aldrich Museum has several educational programs for visitors of all ages.

258 Main St, Ridgefield, CT 06877, Phone: 203-438-4519

Keeler Tavern Museum and History Center


Tour historic rooms and discover colonial stories on an educational weekend visit.

Keeler Tavern Museum and History Center

© Keeler Tavern Museum and History Center

The Keeler Tavern Museum and History Center is a museum and history center in Ridgefield that celebrates over 300 years of the town’s history and heritage. Based in an 18th-century historic building on Main Street, the museum provides an in-depth look at life from the American Colonial era through the mid-20th century in Ridgefield. The home in which the museum is based was summer home to architect Cass Gilbert, who bought the building in 1907 and has since been a farmhouse, a stagecoach stop, a tavern, a post office, and a hotel for travelers. Visitors can enjoy guided tours of the museum while costumed guides accurately portray life in rural Connecticut from the early 18th century to the mid-20th century. Rooms are decorated with period furnishings and feature a variety of ever-changing exhibits, including a cannonball still lodged in an outer wall of the museum. Tours also include the classic Cass Gilbert Garden House, which was built for his wife, Julia in 1915 and features a beautiful brick-walled garden with rose arbors and a reflecting pool.

152 Main St, Ridgefield, CT 06877

Activities and Attractions for Couples and Singles:

ACT of Connecticut


Enjoy Broadway-caliber shows and support local talent on an exciting night out.

ACT of Connecticut

© ACT of Connecticut

ACT of Connecticut is an equity theatre that presents limited engagement runs of well-known Broadway musicals and plays, as well as world-premiere productions by the next generation of writers and composers. All shows feature both Broadway stars and local Fairfield and Westchester County talent. ACT of CT's recent productions have included Stephen Schwartz' "Working", "Evita", and "The 25th Annual Putnam County Spelling Bee." ACT of CT offers expertly-led youth education programs and staged readings of new shows with opportunities for community feedback and involvement. ACT of CT was honored with 11 BroadwayWorld Connecticut Awards in 2018, its inaugural season.

36 Old Quarry Rd, Ridgefield, CT 06877, Phone: 475-215-5433

Ridgefield Theater Barn


Laugh at comedies and see community plays on a fun cheap trip.

Ridgefield Theater Barn

© Matthew Antonino/stock.adobe.com

The Ridgefield Theater Barn is a charming converted dairy barn with heat and air conditioning with 1,000 square foot addition that hosts the Ridgefield Workshop for the Performing Arts, Inc. The family-friendly community theater presents a variety of shows ranging from comedy and drama to musicals that includes a production schedule of four concerts per year performed by a team of raw amateurs and seasoned professionals. The barn theater offers a comfortable, intimate setting with cabaret seating, a reception gallery on the main level, and handicap accessible restrooms. Audience members are allowed to bring their food and beverages to enjoy before the show and during intermission.

Ridgefield Theater Barn, 37 Halpin Ln, Ridgefield, CT 06877, Phone: 203-431-9850

If you are a photographer, don't miss:

Seth Low Pierrepont State Park


Hike wooded trails and paddle the lake on a peaceful retirement escape.

Seth Low Pierrepont State Park

© Al/stock.adobe.com

Seth Low Pierrepont State ParkReserve, also called Pierrepont State Park, is a 305-acre public park that offers a wealth of outdoor recreational activities such as fishing, hiking, mountain biking, and boating. The park is home to five blazed trails include one that winds around the south end of Lake Naraneka, otherwise known as Pierrepont Pond, and the main trail known as the white trail, which runs along Pierrepont Lake ascending from the parking lot to the highest point in the park before descending to a minor entrance. The lake provides excellent hiking and spectacular views of Pierrepont Lake, Redding hills and Long Island Sound can be seen from the top of Barlow Mountain.

50 Barlow Mountain Rd, Ridgefield, CT 06877, Phone: 203-938-2285

What to do if you are traveling with kids:

Bennett's Pond State Park


Explore quiet paths and look at scenic views on an easy spring trip.

Bennett's Pond State Park

© tilialucida/stock.adobe.com

Bennett's Pond State Park is a state park and public recreation area that is home to the 56-acre Bennett Pond, after which it is named. Occupying a portion of the 1,500-acre estate that was once the home of industrialist Louis D. Conley, the park is managed by the Connecticut Department of Energy and Environmental Protection, boasts many miles of hiking trails in a pristine woodland environment and is contiguous with the Wooster Mountain State Park. In addition to hiking in the park and along the Ivy Trail, which crosses through the park, visitors can enjoy fishing, boating, canoeing, mountain biking, and seasonal bow hunting.

550-698 Bennetts Farm Rd, Ridgefield, CT 06877, Phone: 860-424-3000

Weir Farm National Historic Site


Admire artist studios and walk through inspiring landscapes on a romantic couples outing.

Weir Farm National Historic Site

© Weir Farm National Historic Site

The Weir Farm National Historic Site commemorates the life and work of American impressionist painter J. Alden Weir, along with other artists who also lived at the site. One of two locations in the National Park Service devoted to the visual arts, the other being the Saint-Gaudens National Historic Site, the Weir Farm National Historic Site maintain a variety of ongoing artist-in-residence programs whereby artists are hosted at the Weir Farm Art Center for a month-long stay. Set on 60 acres of land, the property is home to 16 buildings, including two restored artist studios, and a hiking trail and tours of the ground are offered National Park Service rangers. Weir Farm also runs an ongoing "Take Part in Art" program, where visitors can create their works at the Weir Farm Art Center.

735 Nod Hill Rd, Wilton, CT 06897, Phone: 203-761-9945

Where to Eat in Ridgefield, CT

  • Bernard’s & Sarah’s Wine Bar – Elegant French dining and an extensive wine list in a cozy, historic setting.
  • TerraSole Ristorante – Upscale Italian cuisine with a creative, seasonal menu and stylish ambiance.
  • Bailey’s Backyard – A farm-to-table bistro serving fresh, locally sourced American dishes with outdoor seating.

If you are interested in local events:

  • Ridgefield Independent Film Festival (May) – Showcasing indie films, live Q&As, and screenings in unique venues around town.
  • Ridgefield Summerfest (July) – Family fun, food trucks, art, and entertainment on Main Street.
  • Holiday Stroll (December) – A festive downtown celebration with caroling, lights, and extended shopping hours.

If you are looking for unique day trips within 30–60 Minutes of Ridgefield, CT:

  • New Canaan (30 min) – Visit The Glass House, tour Waveny Park, and explore upscale shops and dining.
  • Norwalk (40 min) – Check out the Maritime Aquarium or dine along the waterfront in historic South Norwalk.
  • Danbury (20 min) – Visit the Danbury Railway Museum, explore Candlewood Lake, or shop at Danbury Fair Mall.
  • Kent Falls State Park (45 min) – Hike along cascading waterfalls and picnic in the scenic foothills of Litchfield County.
  • Sleepy Hollow, NY (60 min) – Tour the historic cemetery, walk the Hudson River trails, and discover folklore and ghost stories.

Frequently Asked Questions:

  • Q: Where is Ridgefield located?
  • A: Ridgefield is nestled in the foothills of the Berkshire Mountains and is a short drive from New York City.
  • Q: What makes Ridgefield charming?
  • A: The town boasts a unique historical Main Street and an array of activities to enjoy.
  • Q: What outdoor activities can visitors enjoy in Ridgefield?
  • A: Visitors can enjoy a game of golf on the semi-private Fazio-designed 18-hole course or explore hiking and biking trails.
  • Q: Are there opportunities for scenic exploration?
  • A: Yes, Ridgefield offers miles of country roads perfect for exploring the wilderness.

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