The Best Fall Day Trips From New York City

Paddle the Saugatuck River

If you don't own a car—because who does in New York City?—you can take the Metro-North train to Westport, Connecticut (time on the train ranges from 67 to 74 minutes), where you'll be a five-minute walk from Sea Kayak Connecticut, a kayak and paddleboard outfitter located directly on the Saugatuck River.

This tree-lined stretch of waterway is gentle and beginner-friendly, and you can either rent your own boat, book a lesson, or join a guided tour to explore it. In addition to admiring the fall foliage (peaking mid-October) from the water, you may also glimpse certain bird species making their annual migration. Experienced paddlers may want to head downriver to explore islands in the Long Island Sound.

Go on a Safari at Action Wildlife

Action Wildlife is a 116-acre zoo and museum located two hours northeast of New York City in Goshen, Connecticut. This outdoor park is an affordable family adventure where you can meet an oryx, stare down a water buffalo, watch bison roam, see a moose, or feed a deer. Main attractions include the drive-through safari, petting zoo, and on select days during fall, hayrides through the property. More than 350 exotic animals call Action Wildlife home, but you can only see them from spring through fall as the animals need to be sheltered during the colder months. It will be open every weekend, Friday through Sunday from 10 a.m. to 3 p.m., during fall 2020.

Although it will add about 40 minutes each way to your trip, driving Route 7 through Ridgefield and Kent, Connecticut, is the most picturesque way to go.

Get Outside at the White Memorial Conservation Center

Litchfield, Connecticut, with its antique shops, galleries, scenic roads, and rolling hills, is one of the prettiest places in New England come fall. This is home to the White Memorial Conservation Center, comprising 4,000 acres of spectacular foliage, a nature museum, campgrounds, 40 miles of hiking trails, a portion of the Bantam River (plus several ponds), and a gift shop to kick off your holiday shopping.

You can spend an entire weekend here renting kayaks from the marina and drifting along the river, hiking up Apple Hill to get a bird's-eye view of the fall foliage, and spotting wildlife in the Catlin Woods. The grounds are open 24 hours a day, year-round, but the museum and gift shop are only open Monday through Saturday from 9 a.m. to 5 p.m., and Sundays from noon to 5 p.m. (At the beginning of the 2020 fall season, the museum remained closed.)

If you happen to venture out to Lichfield on a Sunday, consider making brunch reservations at the White Horse Country Pub & Restaurant in nearby Marbledale.

Be Inspired at Chesterwood

A day trip to Chesterwood, the former studio and home of renowned sculptor Daniel Chester French, starts with a scenic drive from New York City to the Berkshires of Western Massachusetts. The 122-acre estate and museum, now looked after by the National Trust for Historic Preservation, features both rotating exhibitions and a permanent collection by French himself, who is most famous for crafting the Lincoln Memorial in Washington, D.C.

Located in Stockbridge, Massachusetts (a two-hour, 45-minute trip from NYC via the Taconic State Parkway), Chesterwood typically stays open for the season until the end of October. You'll see nearly 500 models, studies, and full-size sculptures on exhibit in the studio, museum, gallery, and gardens. While you're in Stockbridge, plan a lunch or dinner at the Red Lion Inn, a Stockbridge landmark since 1773.

Tour America's Oldest Winery

Brotherhood Winery in Washingtonville, in the foothills of New York's Catskill Mountains, is an ideal day trip destination for wine lovers who want to escape to the country. Time your trip right and you'll see the local trees in their full autumn splendor, typically around the end of September or early October.

Established in 1839, Brotherhood is the oldest continually operating winery in the U.S. Although tours through the property have been canceled for much of 2020, the tasting room will be open by reservation (and to six people at a time) during fall. Apart from sampling a wide variety of award-winning vino, you'll also be able to explore the shops and restaurants on the winery grounds.