The 10 Best Fall Day Trips From New York City

Spooky season is alive year-round in this Hudson Valley town, the inspiration for Washington Irving’s eerie tale of “The Legend of Sleepy Hollow.” Irving is actually buried in Sleepy Hollow Cemetery, a massive resting place known for hilltop fog, historic gravesites, and lush fall foliage. You can venture over to the Headless Horseman Bridge and tour the historic Philipsburg Manor before making your way over to adjacent Tarrytown. Their main street features unique stores (think: a whole house filled with antique finds called Pretty Funny) and great restaurants, including Horsefeathers Tavern. Literature-themed murals and eclectic decor make this the perfect place to grab a bite.

An hour and 30-minute train ride from Grand Central Terminal will leave you in Beacon, a vibrant city known for markets, nature preserves, and art galleries. To be clear, Sundays here are for shopping. The seasonal Beacon Flea Market is open from April through November and houses over 50 mom-and-pop vendors; the same goes for The Beacon Farmers Market, where you can purchase fresh, locally-grown produce. And if you’re trying to shop for antiques, you’ll be spoilt for shop choice on Main Street with places like Blackbird Attic. This city is also home to several eclectic museums, with the most notable being Dia Beacon.

Book lovers need to prioritize a visit to Niantic, Connecticut. It’s a bit of a trek from Manhattan (around three hours with a car), but it’s absolutely worth the drive for one thing: Book Barn. This is a sprawling “bookstore” spread over individual sheds that house thousands upon thousands of gently used novels. Each barn is themed, with new arrivals held in “Ellis Island,” while “The Underworld” is covered in gargoyle decor and plays home to spooky books. There’s even a farm area with goats! Finish off the day with shopping (Anna Pearls Curiosities is home to great vintage pieces), a fall-approved cider at Niantic Public House and Brewery, or opt for homemade candies and ice cream at the 1950’s-inspired Gumdrops & Lollipops.

Although its name has become synonymous with the iconic 1969 music festival, Woodstock is an ideal day trip for folks in need of relaxation. You can hike along the trails of Overlook Mountain or leisurely stroll along the Ashokan Reservoir pathways before making your way to Tinker Street for hot chocolate at Bread Alone. If you’re looking for other snacks, the local Woodstock Farm Festival runs every weekend and offers everything from mushrooms and ice cream to fresh eggs and cheese.

Philadelphia is shockingly close to Manhattan: two hours via car and an hour from Penn Station, making it the perfect day trip for folks who prefer large cities (but want a brief break from New York). History buffs will love visiting the Liberty Bell, the Betsy Ross House, and Independence Hall, while Philadelphia’s Magic Gardens gallery provides a feast for the eyes. Schedule free time to wander throughout Wissahickon Valley Park for prime fall foliage, then be sure to stop by Elfreth’s Alley Museum, a quaint cobblestone street that’s recognized as a National Historic Landmark.

This quaint New Jersey town is a prime destination for October. Why? It’s home to AddamsFest. Charles Addams, the cartoonist behind the Addams Family, was born in Westfield and even modeled the iconic spooky mansion after a house he saw on Elm Street. Homage is paid to the franchise throughout the month of October—the city is splashed with murals inspired by Addams’ macabre characters, storefront windows are decorated, there are masquerade balls, cartooning workshops, pumpkin carvings, and a house decorating contest.

Add Peconic to your fall bucket list if you’re looking for a boozy day filled with vino and cheese. This quaint county is located on the North Fork of Long Island and is home to dozens of wineries, including Pindar Vineyards, Osprey’s Dominion, and Raphael. You can book a day tour that provides roundtrip transportation from central Manhattan and an organized itinerary with stops at multiple vineyards, making it an easy (and super fun!) activity for a large group of friends.

Fall foliage is guaranteed with a visit to New York’s Hudson Highlands, particularly at Bear Mountain State Park. The park is home to multiple trails that zigzag through a lush canopy of colors that range from beginner-friendly to difficult hiking paths. And if you’re not into hiking, no worries: you can book an Oktoberfest-themed day cruise that includes panorama scenic views, delicious food, live music, and craft beer. It departs from Pier 83 in Manhattan, cruises up the Hudson, and makes a two-hour stop at Bear Mountain.

New Haven’s reputation is rooted in perhaps the most important food group: pizza. This quaint New England town is known for its riff on New York-style pizza, with a thinner charred crust and less cheese that produces a crunchier texture. Two iconic spots to visit are Frank Pepe Pizzeria and Sally’s Apizza; have one for lunch and one for dinner so you can compare the two. Between carbs, you can visit Yale University and ride the Carousel at Lighthouse Point Park.

Breathtaking hikes and scenic drives await in the Catskills, with gorgeous views throughout Mount Utsayantha, Hunter Mountain, Walnut Mountain Park, and the Catskill Mountains Scenic Byway. Take a break by sampling crisp hard cider at Hudson Valley Farmhouse Cider or Bad Seed and if you’re contemplating an overnight trip, consider booking a Getaway. It’s a series of tiny homes with comfy, oversized beds and floor-to-ceiling windows that provide unobstructed foliage views.