Coastal Western Connecticut

While Greenwich is most famous for its shopping, this coastal town also offers much waterfront beauty. Take a stroll on Island Beach or at Byram Shore Park, where you can also take a refreshing dip in the pool, or rent a sailboat, kayak, or paddleboard for on-the-water fun at Greenwich Community Sailing.

Head over to Greenwich Harbor for a mouthwatering meal at l’escale (with marina views, of course) or indulge in a spa treatment at Delamar Greenwich Harbor. Discover more spots to eat, stay, and play in Greenwich below.

For the perfect mix of vibrant city and beautiful coast, Stamford is a fantastic choice. Harbor Point District, located immediately south of Downtown Stamford, is a 100-acre waterfront destination filled with shopping, parks, marinas, foodie finds, and a rotating schedule of events. Try photo-worthy food creations at Elm Street Diner or decadent dinner at Prime, and end the night watching the sunset on Sign of the Whale’s rooftop patio (with a drink in hand, of course).

On the waterfront, enjoy free water taxi rides across the channel or rent paddleboards, kayaks, go on a sail and more at SoundWaters. Free shuttles and trolleys make for an easy (and fun) way to get around. Discover more places to eat, stay, and play in Stamford here, or check out the spots below.

The coast just isn’t the coast without picturesque lighthouses. In Norwalk, board a Sheffield Island Lighthouse Tour, Harbor Cruise, or Sunset Cruise to connect with history and nature. You may even have time to picnic on Sheffield Island. Then head to Calf Pasture & Shady Beach for sun, sand, boat rentals, boardwalks and shops. Or take the kids to the Maritime Aquarium to come nose-to-nose with sharks, seals, river otters, sea turtles, and more!

When the sun goes down, you’ll find plenty of night life and culinary adventures in Downtown SoNo (South Norwalk).  If you time your trip just right, you can attend the annual Norwalk Oyster Festival. Find more places to explore, eat, and stay here or check out the spots below.

Home to Compo Beach and Sherwood Island State Park, Westport offers plenty of ways to get your beach day fix – whether you prefer saltwater swims or picnics in the soft sand. Want to get out on the water? Longshore Sailing School offers sailboat, kayak, and paddleboard rentals.

After you’ve washed the sand from your toes, discover fantastic downtown shopping with big box favorites and smaller boutiques in Downtown Westport. Grab a bite amongst the vines at Terrain Garden Café or get right by the water at Black Duck Cafe or La Page.

At night, see a live show along the Saugatuck River at Levitt Pavilion, which produces one of the largest and longest-running free outdoor festivals in the nation. Find more places to eat, stay, and play in Westport below.

If you’re stopping through Milford, Walnut Beach and Silver Sands State Park are the perfect spots to enjoy sun, surf, and fishing. Then add some extra adventure to your day by renting kayaks, SUPS, bikes and motor scooters from Scoot & Paddle.

Plan a trip during August to attend the annual Milford Oyster Festival. Voted the best food festival in Connecticut by National Geographic, the festival features 30,000 oysters, all of which are harvested in Milford waters, as well as craft beer and wine, and a full lineup of entertainment. Explore more spots to eat, stay, and play in Milford below.

Discover coastal towns in Eastern and Central Connecticut to create the ultimate Coastal Connecticut road trip!