Downsizing Help in Fairfield County CT

Home to some of the nation’s rich and famous, Greenwich has more to offer than just a Back Greenwich mansion tour and polo matches at the Greenwich Polo Club. Downtown Greenwich on “the Ave”, or Greenwich Ave, is the place to be with shopping, spas, and art galleries; including the Bruce Museum of Arts and Science. Situated along the coast, Old Greenwich is an old beach town that is the home of Greenwich Point Park beach, downtown shopping, and Binney Park. The Cos Cob neighborhood, which hugs the Mianus River, is the birthplace of the Boy Scouts at Pomerance Park. It is also home to Connecticut’s first art colony at the historic Bush-Holley House. When you’re hungry, head to local favorites Lugano, Le Fat Poodle, or Applausi in Old Greenwich or Tony’s at the J House in Riverside.

East of Greenwich on the coast is Stamford where you can enjoy the outdoors at the Cove Island Park beach with its amenities, the quiet West Beach, a carousel and ice rink at Mill River Park, and the boardwalk, boat launch, and fishing pier at Cummings Park. Stamford’s performing arts culture is thriving with the Stamford Center for the Arts, Curtain Call, and Avon Theatre. Stamford’s antique district is home to three of the top antique shops in the state: Hamptons Antique Galleries, Avery & Dash Collections, and Stamford Modern. For great eats head to Lorca or Sergio’s Pizza Restaurant.

Further up the coast is Darien, where you can enjoy the ocean at Pear Tree Point Beach and Weed Beach or other nature sights at Chery Lawn Park and Tilley Pond Park. Local attractions include the Salt Cave of Darien, the Mather Homestead, and the Geary Gallery. If you’re hungry you’ll enjoy local restaurants Ten Twenty Post for their oyster bar, the Goose American Bistro & Bar, or the Sugar Bowl Luncheonette. Then wash it all down with a craft beer at the Lock City Brewing Company.

North of Darien is New Canaan, which is home to some unique buildings: The River house at Grace Farms designed by the Pritzker Prize-winning Japanese architecture firm SANAA, The Castle Elizabethan-style mansion in Wavenly Park commissioned by one of the founders of Texaco, and last but certainly not least, the Philip Johnson Glass House that has glass walls everywhere except the bathroom. You can take in other types of art at the Carriage Barn Arts Center and Silvermine Arts Center. For a local treat, order an ice cream cone at Gofer’s. 

Further up the coast is Norwalk, where the South Norwalk Historic District, SoNo, stands out with its historic buildings, local shops, waterfront views, the SoNo Switch Tower Museum, and local eateries and watering holes like the SoNo American Craft Distillery and SoNo Seaport Seafood. Also in Norwalk is the Maritime Aquarium, Lockwood-Mathews Mansion Museum, Norwalk WPA Murals, and Stepping Stones Museum for Children. You can enjoy the view of the quaint Sheffield Island Lighthouse from Bayley Beach in the affluent Rowayton neighborhood or take the ferry out to see it up close.

North of Norwalk you will find Wilton, where there are plenty of outdoor parks and historic sites, such as the Weir Farm National Historic Site, the Norwalk River Valley Trail, the Woodcock Nature Center, Ambler Farm, the Gallaher Mansion and Cranbury Park, and the Richard Foster House, or Round House. Also of interest is the Wilton Playshop, local brewery Little Pub Wilton and restaurants Marly’s Bar & Grill and Naked Green’s. 

East of Norwalk on the coast is Westport, where the main attraction are all the water activities, including Compo Beach. Westport has a thriving arts community with the Westport Country Playhouse, Levitt Pavilion for the Performing Arts, and Westport Arts Center. Also of interest is the Westport Astronomical Society observatory.

Further along the coast to the east is Fairfield, where the beaches of Jennings Beach, Penfield Beach, Southport Beach, and Sasco Beach are the main draws. You can take in the local history and art at the Fairfield University Art Museum, the Quick Center for the Arts, the Fairfield Museum and History Center, and the Old Post Road Historic District. Check out local eats at Wild Rice, Barcelona, and great gluten-free pizza at Colony Grill.

Bridgeport is Connecticut’s largest city and boasts many attractions, such as the state’s only zoo, Beardsley Zoo and The Barnum Museum featuring its famous former resident P.T. Barnum. Choices for taking in a game include the Bridgeport Bluefish baseball team, the Sound Tigers hockey team, or the Fairfield University NCAA basketball teams. Bridgeport is also a great place to enjoy the arts with the Housatonic Museum of Art or dinner and a show, where you can start at Ralph-n-Rich’s for some local seafood then head over to the Downtown Cabaret Theatre or the Webster Bank Arena.