Ready to get outside? Fairfield County is packed with places to paddle, pedal, and hit the trails—and if you’re up for a little extra drive, nearby towns in Connecticut and New York have even more outdoor adventures waiting.
Where to Kayak
- Sherwood Island State Park (Westport)
Launch your kayak from Connecticut’s first state park and paddle along the Long Island Sound. Calm waters and scenic views make it a perfect day on the water.
Sherwood Island Connector, Westport
- Saugatuck River (Westport)
Adventure starts right downtown! Glide under bridges, past waterfront homes and out toward the Sound. Rentals are available nearby.
Launch from Parker Harding Plaza, Westport
- Five Mile River (Rowayton/Norwalk)
A charming, calm route lined with classic New England views—great for a sunset paddle.
Launch from Rowayton Avenue Boat Ramp, Norwalk
- Greenwich Point Park (Old Greenwich)
Paddle along beautiful Tod’s Point—ideal for beginners thanks to calmer waters.
11 Tods Driftway, Old Greenwich
- Weekend Kayak and Paddle Board Rentals (Stamford)
Enjoy kayaking or paddleboarding on the Long Island Sound from Stamford’s SoundWaters Harbor Center.
Cohen SoundWaters Harbor Center, Boccuzzi Park, 200 Southfield Ave, Stamford, CT
Bonus Nearby:
Croton Point Park (Croton-on-Hudson, NY)
Paddle the Hudson River with beaches, hiking trails and if you want to make it an overnight trip. There are campgrounds.
1 Croton Point Ave, Croton-on-Hudson, NY
Where to Bike
- Norwalk River Valley Trail
A growing paved and crushed stone trail through Norwalk, Wilton and beyond. Family- and beginner-friendly.
Best access: Mathews Park, 295 West Ave, Norwalk
- Fairfield Rail Trail
Flat, easy, and perfect for casual rides—connecting neighborhoods, parks and even the beach.
Start at Mill Plain Road near the Fairfield Metro train station, Fairfield
- Mianus River Park (Stamford/Greenwich)
A wooded wonderland packed with mountain biking trails.
Entrances: Merriebrook Lane, Stamford or Cognewaugh Road, Greenwich
Bonus Nearby:
Old Croton Aqueduct Trail (Westchester County)
Bike an historic, shaded trail from Yonkers to Croton—a great mix of nature and small towns.
Access from 15 Walnut St, Dobbs Ferry
Where to Hike
- Devil’s Den Preserve (Weston/Redding)
Over 20 miles of trails through shady woods and past scenic overlooks.
33 Pent Road, Weston
- Bartlett Arboretum (Stamford)
Peaceful gardens and short forest hikes—perfect for a relaxing outdoor day.
151 Brookdale Road, Stamford
- Weir Farm National Historical Park (Wilton/Ridgefield)
Walk the trails that inspired America’s famous landscape painters.
735 Nod Hill Road, Wilton
Bonus Nearby:
Ward Pound Ridge Reservation
Westchester’s largest park with 35-plus miles of hiking trails through meadows woods and streams.
Route 121 South, Cross River
Quick Tip: Always check parking info and trail conditions before you go.