10 Fall Road Trips Within Two Hours of NYC
NYC is undoubtedly lovely this time of year, but something about the autumnal air makes us want to get out of town. And whether you’re in the market for a bucolic retreat, a quaint hamlet or even just a (different) bustling city, these not-so-far-flung destinations are more than worthy of digging out that driver’s license. Here are ten exciting fall road trips near NYC.
1. Litchfield Hills, Connecticut
Litchfield is known for some of the best antique shopping in Connecticut, so if scouring estate sales, curated barns-turned-stores and flea markets for vintage gems is your jam, this getaway is right up your alley.
Stay: Book a stay at Winvian Farm, which boasts 18 luxury cottages each with its own unique spin—like a whimsical-chic tree house, a refurbished helicopter and a nautical lighthouse.
Do: Don’t feel like going far? The resort offers horseback riding, cooking classes, bikes for guests and a luxurious spa, along with snowshoeing and cross-country skiing come the winter months. If you’re feeling ambitious, you’re just a quick ten-minute drive from hot-air ballooning.
Eat: Sample the “seed-to-table” tasting menu at Winvian’s onsite restaurant, or head to the West Street Grill for bistro-style eats (the Parmesan aioli peasant bread is a must) and alfresco seating.
2. Princeton, New Jersey
Though you could spend an entire day touring the campus of Princeton University—full of Gothic architecture that looks increasingly spooky as Halloween rolls around—the Ivy League college is not the only thing of note in this charming town.
Stay: If you want to be within walking distance of all the action, look no further than Princeton’s Palmer Square and focal point The Nassau Inn, a historic landmark hotel where Thomas Paine and Paul Revere hung out.
Do: Princeton has a pedestrian-friendly shopping district full of clothing stores, home décor outposts and a few old-school bookstores with killer names, like Labyrinth Books and The Cloak & Dagger, which is dedicated to mystery books. There’s also a cupcakes shop that would give Magnolia a run for their money any day. Drama buffs should be sure to catch a show at the venerated McCarter Theatre Center.
Eat: You could easily spend the better part of your weekend eating your way through town, from the casual and aptly-named PJ’s Pancake House to the elegant Peacock Inn, which is housed in an adorable Victorian-era home and doubles as a boutique hotel. Agricola Eatery is a local’s favorite and is filled with good design and vibes. Whatever you do, do not skip out of town without trying the unique ice cream creations at The Bent Spoon, a local favorite.
3. Philadelphia, Pennsylvania
Sure, the Liberty Bell and Independence Hall are worth seeing if you’ve never been, but you’ll also want to leave enough time for incredible food and a creepy prison tour.
Stay: Aloft Philadelphia Downtown blends the city’s rich history with contemporary vibes. The 179 guest rooms took over the former Liberty Title & Trust Building, built in 1925. If you want to go full-on fancypants, the Four Seasons Philadelphia is a contemporary marvel of design, architecture, and views.
Do: Take a relaxing stroll through Philly’s famed Rittenhouse Square: It’s a great place to take in the fall colors as you admire the beautiful homes built around it, some of which date back to the early 19th century. The iconic LOVE Park is a must, as are the pseudo-psychedelic Magic Gardens, if even only for the Instagram opportunity. And those inclined to the macabre need to make a stop at Eastern State Penitentiary, the historic prison where Al Capone was once incarcerated which is extremely popular around Halloween for obvious reasons.
Eat: Even the snobbiest New Yorkers won’t be disappointed in Philly’s thriving dining scene, where yes, even the pizza is good. Try eeva or Down North if you’re in the mood for ‘za. The latter has an incredible mission to reduce recidivism, and exclusively employs formerly incarcerated people and pays them equitable ages.
4. Bedford, New York
No wonder Blake Lively and Ryan Reynolds once chose to settle down in this quaint Westchester town—it’s close to the city while still maintaining plenty of rural charm.
Stay: Check into the Bedford Post Inn, an eight-room property (with romantic fireplaces in most rooms) that features two incredible restaurants—one with a see-and-be-seen outdoor patio—and a yoga studio.
Do: Spend a nature day at Ward Pound Ridge Reservation; the nearby Outhouse Orchards for Halloween-esque corn mazes, spooky hayrides and pumpkin picking; and Rainbeau Ridge for playing with animals and savoring local cheeses.
Eat: The Bedford Post’s onsite eateries mean you don’t have to venture far: Try The Barn for country classics and a killer brunch, or the lively Bedford 234 where avocado fries, flatbreads, a burger, and wildly good brown butter sugar pie are menu highlights. For fine diners, The Inn at Pound Ridge by Jean-Georges is just down the road from Bedford and housed in a beautifully restored and now luxe 1800s home that is the ideal spot for special occasions.
5. New Canaan, Connecticut
This idyllic town is an hour and a half from Manhattan and offers everything one might need or want for a long weekend: historic landmarks, fall foliage sightings, adorable B&Bs and upscale boîtes (that you don’t have to wait hours to get into).
Stay: Reserve a room at Graybarns Inn, the rustic-meets-cozy refuge that overlooks the Silvermine River and Guthrie Pond. The property is the kind of place you visit in the fall to relax and unwind in a stunning natural setting. GrayGoods, the carefully curated on-site mercantile, is a place to drop some cash on luxe, artisanal items.
Eat: There are plenty of places to sit and eat in NC’s adorable downtown, but a standout is South End, where comfort food reigns supreme and the cocktails are always on point. The seasonal salads and outrageously good burger at Elm Restaurant will have you making return trips on Metro-North just for the food.
6. Nyack, NY & The Hudson Valley
Nyack is a great home base if you’re looking to explore points north in the Hudson Valley—or you just need the closest possible jaunt outside NYC.
Stay: Check in to Hotel Nyack to enjoy the hotel’s trendy, luxe loft-style rooms filled with bold print wallpapers, chandeliers, and other fun design details. The pet-friendly hotel also boasts a buzzy local food and nightlife scene, which centers around contemporary steakhouse The Grille at Nyack and its aged steaks in a handsome, open-aired indoor space and patio.
Do: Just across the river you’ll find the Lyndhurst Mansion in Tarrytown, a Gothic Revival mansion with a noteworthy history, and the historic village of Sleepy Hollow, which—naturally—ramps up the spooky spirit every October.
7. Asbury Park, NJ
Asbury Park may be on your radar as a summertime spot, but this funky resort town—and its somewhat gritty past—is having a major resurgence, making it a great year-round destination.
Stay: You’ll want to hang your hat at The Asbury, which was converted from a former Salvation Army building into a hip beachside hotel and has beautifully designed rooms and cool lounge spaces throughout. It’s also a great place to enjoy one last alfresco cocktail before the weather gets too cold, at Salvation, the rooftop garden bar. During the fall months, you can also score a deal on the fab rooms at the pricey-in-the-summer-but-totally-worth-it Asbury Ocean Club.
Do: Catch a show at the legendary dive, The Stone Pony where Springstein and Bon Jovi played. Or get acquainted with Asbury’s lively LGBTQ scene with a drag show at Paradise, located at the Empress Hotel.
Eat: Grab lunch at Porta, a wood-fired pizza joint and beer garden (though be forewarned, it turns into a Jersey Shore dance club at night).
8. POUGHKEEPSIE, NY
Poughkeepsie hasn’t historically been as popular with Hudson Valley travelers—in part due to its size. It feels more like a small city than a cute, river-adjacent town. Recently, an influx of pandemic transplants has influenced new energy, and it’s quickly becoming a favored stop for those exploring the region. We also love it because it’s not as car-dependent, and you can easily access it by train from Grand Central.
Stay: The Hyatt Place Poughkeepsie wins points for being generally new, having clean, contemporary rooms, and budget-friendly rates for those visiting the Hudson Valley during its primo fall season, when prices can be through the roof.
Do: Part of what makes the Hudson Valley an intriguing destination is the numerous spots to take in breathtaking views of the Hudson River and the surrounding mountains and greenery. One such spot where you absolutely must stop is The Walkway Over the Hudson. Exactly as it sounds, it offers visitors the chance to lock arms and walk across a former cantilever and truss railroad crossing that projects over the Hudson River, while exposing some of the area’s most spectacular views. North of Poughkeepsie in Hyde Park, history buffs can see another popular local tourist attraction: Franklin D. Roosevelt’s home and estate as well as the Franklin D. Roosevelt Presidential Library; both are open to the public for a $10 admission fee.
Eat: Essie’s restaurant is consistently rated high by locals and travelers alike; it puts out delicious proteins but also has great options for vegetarians and vegan diners as well. If you visit on a Wednesday, they also serve a special “waffles n’ wedges” menu consisting of regular waffles, chicken and waffles, and potato wedges that will knock your socks off.
9. The Poconos, Pennsylvania
With forested peaks, shimmering lakes and lush valleys, there’s something truly magical about the Pocono Mountains in northeastern Pennsylvania, especially during the autumn months when leaf-peeping opportunities abound. Oh, and did we mention that all of this natural beauty and adventure lies just two hours away from the city?
Stay: The Poconos area is vast, so you’ll likely want to pick one of the many charming small towns in the area and make that your base for exploring. Stroudsburg is a popular choice for its bustling downtown but if you want to be close the action while enjoying some peace and quiet, beautiful Mountain Springs Lake Resort is just the ticket. And for moms, we’re excited about the Diva Moms gratitude getaway in Tyler Hill Camp this November 19 to 21. Set on two private lakes, this fall excursion is a much-needed break for the hardest working members of the family with activities such as meditation, hiking and Thanksgiving cooking demo's planned...plus plenty of relaxation, of course.
Do: Outdoor enthusiasts will love hiking, fishing and skiing in the Poconos, while history buffs can explore the area’s museums and sites, including the No. 9 Mining Museum and Lehigh Gorge Scenic Railway. For families, there are multiple water parks worth exploring such as Camelback Lodge and Aquatopia. Whatever you do, make sure you take time to sit back and take in the gorgeous scenery.
Eat: For the Diva Moms getaway, all meals will be prepared and served in the serene setting, with the option to bring all the alcohol you want to add to your weekend (we’ll cheers to that). In Stroudsburg, we love Sweet Creams Cafe’s hearty sandwiches for lunch and Sarah Street Grill’s eclectic menu for dinner.
10. NEW HOPE, PA
In New Hope, you can grab a pumpkin spice latte at Starbucks (they’re post-cheugy at this point anyway), which is housed in a historic building and as close to a chain experience as you’ll find in the Delaware riverfront town. The vibrant, eclectic community is otherwise filled with unique craft and artisanal shops, great art, handsome eateries, and pique fall charm.
Stay: An intimate, 12-room boutique hotel with views of the Delaware River, we promise The Ghost Light Inn isn’t haunted. Instead, the property’s name is influenced by its location, adjacent to the Bucks County Playhouse, and a superstitious reason many theaters leave a light bulb lit on their stages. Rooms here each include their own ghost light, plus textured wood paneled walls, bathrooms with double vanities, and posh beds with nail head headboards.
Do: Shopping the compact, charming streets of downtown New Hope will inspire you to come back each season, as will taking in one of the quality shows at the aforementioned Bucks County Playhouse. The adorable theater is oozing with charm since it’s housed in a former grist mill. You can take a scenic train ride, explore historic buildings like the Parry Mansion, or get out into the stunning nature that surrounds this town during the fall at Solebury Orchard. And yes, they have all the apple picking, cider, and donuts you have your heart set on. On a nice day, a slow-paced stroll along the Delaware Canal or a short walk over the charming New Hope-Lambertville Bridge (which connects an equally charming NJ town) is not just recommended, it’s pretty much required.
Eat: The town’s Ferry Market is a place you show up to on an empty stomach. Home to delightful vendors using ingredients straight from local farms, it’s the kind of place where you might find a Peruvian empanada or Venezuelan arepa, macaroons, a vegan butcher, a smorgasbord of meat and cheese, a wine flight, and a beer tasting—all in the same gorgeous space. For a more formal, sit-down meal, Stella’s of New Hope creates Insta-worthy dishes, and the grub and ambiance at Salt House is always a hit. It will perfectly match the comfy cozy fall vibe you’ve got going on in your favorite flannel or leather jacket.
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