13 Fall Road Trips Near NYC for All Your Leaf-Peeping, Apple-Picking and Wine-Sipping Needs

• Distance from NYC: approximately 217 miles or 3 hours, 30 minutes by car (or take a high-speed Acela and ditch car dependency altogether) 

Maybe it's the crisp air, the changing leaves, or the pumpkin spice, but we can't get enough of Beantown in autumn. Strolling through the Public Garden this special time of year is especially lovely as the trees start to change color and the flowers are still in bloom. 

Stay: Timeless and effortlessly chic, Boston Harbor Hotel is positioned on Rowes Wharf and gives travelers the best of both worlds—the Boston Harbor and the Boston cityscape. Traveling with your four-legged pal? This pretty accommodation is also a great pet-friendly option.  

Other stays we love:

• South End Studio near T, Shops + Dining
• 907 Main Square
• Green Turtle I Houseboat in Boston Harbor 

Eat: Esteemed chef Lydia Shire (a friend to the late, great Julia Child) has helmed Scampo, located at The Liberty Hotel, since 2008 where highlights include a large Kurobuta pork chop, a lobster and lamb-topped pizza, green bean tempura, and a well-worth-the-carbs naan bread. For seafood, visit Bank’s Fish House (save room for the Banana Ice Cream Sundae) or snag a sunset table at the more casual The Barking Crab, a shucker house that will fulfill any cute and casual seafood extravaganza fantasy. 

Do: Previously covered in parking lots, Seaport neighborhood has been transformed with glittering, modern skyscrapers, cute cafes and restaurants, upscale shops at The Superette and great museums, like the Institute of Contemporary Art (ICA), where Yayoi Kusama’s otherworldly “Love Is Calling” is currently on display. The neighborhood is also home to Cisco Brewers, a newly opened green space The Rocks at Harbor Way. You can also explore classic Boston by following the Freedom Trail; sure, it’s one of the most popular tourist attractions in Boston, but that’s for good reason. The 2.5-mile long walking trail takes you to 16 different historical sites, including the Paul Revere House, the Old State House, and Fenway Park. It's a great way to see the city and learn about its rich history—plus, it’s free and it’s a sneaky way of doing a walking tour without needing to look at a map (though you can). Simply follow the red brick in the trail all around the city to see some of its best sites. 

• Distance from NYC: approximately 106 miles or 2 hours by car (or take the LIRR)

Leaf peeping season is something to behold in Amagansett where you can catch some of autumn's most vibrant foliage—and the best part is, this quaint Hampton’s hamlet sees a steep decline in tourism after summer, so you won't have to deal with overwhelming crowds.

Stay: The ultra-cozy Roundtree Hotel is uniquely composed of centuries-old renovated cottages and a barn. If you spring for a cottage, you can even enjoy warming up by a private fireplace beneath an airy cathedral ceiling (one cottage dates back an astonishing 250 years). 

Other stays we love:

• Contemporary Home with Furnished Deck 
• Ms Alcott 

Eat: Wölffer Kitchen Amagansett is an upscale bohemian eatery owned by Wölffer Estate Vineyard, and it’s considered one of the hottest dining spots in the Hamptons no matter the season. For a more casual dining experience, Main Street Tavern serves classic American fare from a balanced menu of seasonal and savory dishes like crispy shrimp, zucchini fritters, and homemade chicken pot pie. It’s also a great place to have a beer and watch the game.

Do: Drive over to Hank’s Pumpkintown for some of the best seasonal activities around like apple picking, pumpkin picking, and braving some of Long Island’s most intricate corn mazes. When you get hungry, stop by The Market for fresh pies, apple cider slushies, and other sweet treats. If you like to go off the beaten path, you can take a self-guided hike through East Hampton’s historic ghost town, an abandoned “northwest settlement” that dates back to the 17th century. When you’re ready to return to civilization, stroll through Amagansett Square where you’ll find lovely boutique storefronts, eateries, wellness shops, and more at the heart of the friendly town.

• Distance from NYC: approximately 135 miles or 3 hours by car (or take Amtrak)

During the fall, the picturesque town of Mystic, Connecticut combines an enchanting downtown, urban comforts, and brilliant autumnal hues with coastal charm. Founded in 1665, the historic site is a significant Connecticut seaport with more than 600 ships built over 135 years. There’s plenty to do and see, from the Mystic Seaport Museum (the largest maritime museum in the U.S.) to the downtown waterfront shopping district that boasts over 80 independently-owned shops and fine art galleries. 

Stay: Whaler’s Inn offers a warm respite from fall’s cold temperatures in the heart of Mystic, just steps from the banks of the Mystic River and the Bascule Drawbridge. Featuring 45 well-appointed rooms with understated historical charm, the five-building complex dates back to 1910. During colder months, the lobby awaits with an ever-crackling fire and complimentary fresh-baked afternoon cookies. 

Other stays we love:

• Mystic's Guesthouse in Historic Downtown Waterfront District 
• Mystic Countryside Farm 

Do: Mystic Country is part of both the Connecticut Wine Trail and the Coastal Wine Trail, offering pleasurable tours through some of the finest vineyards on the East Coast. Travelers have an abundance of wineries and vineyards to choose from (Saltwater Farm Vineyard draws visitors year-round for its beautiful tasting room, uniquely located in a WWII-era private airport), but no seasonal stay would be complete without stopping by B.F. Clyde’s Cider Mill. Founded in 1881, it’s the oldest steam-powered cider mill in the U.S., offering delicious wines and traditional ciders that are taken directly from the barrel to the jug for a rich, oaky flavor. Spider Cider is a fan favorite, best served in a hot toddy with a side of B.F. Clyde’s famous old-fashioned cider donuts. 

Eat: Grab a slice of wood fired pizza at Mango’s or indulge in a steaming cup of coffee and spooky artisanal donuts—the pumpkin chai is super cute—at Deviant Donuts. Captain Daniel Packer Inne is a short stroll from Main Street in Downtown Mystic, offering cozy inn ambiance in a restaurant that was built over 250 years ago. You’ll love their comforting soups including baked onion and clam chowder, all prepared with the freshest quality ingredients. Be sure to stop by Mystic Pizza while you're here too, a nostalgic spot that serves up pies in a space filled with memorabilia. Yes, it did inspire the 1988 film and yes, the iconic pizza really is a slice of heaven!

• Distance from NYC: approximate 99 miles or 2 hours by car

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.

Other stays we love:

• Your Escape to the Hills
• Cozy Litchfield House w/ Fenced-In Yard & Fire Pit 

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.

• Distance from NYC: approximately 53 miles or 1 hours, 15 minutes by car (also reachable via NJ Transit)

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.

Other stays we love:

• Spacious 2 BR Central Princeton Home w/ Parking 
• Top-Floor Princeton Condo with Private Balcony 

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 favorite and is filled with good design and vibes. And whatever you do, do not skip out of town without trying the unique ice cream creations at The Bent Spoon.

• Distance from NYC: approximately 95 miles or 1 hour, 15 mins by car (or, take a high-speed Acela)

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.

Other stays we love:

• The Witherspoon 
• Charming One Bedroom by Rittenhouse Square 

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.

In Philly, you can also grab a table at the buzzy Vetri for Italian, El Vez for Mexican, and River Twice for a little bit of everything.

• Distance from NYC: approximately 47 miles or 1 hour, 15 minutes by car 

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.

Other stays we love:

• The Witherspoon 
• Charming One Bedroom by Rittenhouse Square 

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.

• Distance from NYC: approximately 47 miles or 1 hours, 15 minutes by car

This idyllic town is less than 90 minutes 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.

Other stays we love:

• The Witherspoon 
• Charming One Bedroom by Rittenhouse Square 

Do: Between The Glass House, Grace Farms and Waveny Park, the area’s a dream for anyone who loves architecture and landscape design.

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.

• Distance from NYC: approximately 2 miles or one hour by car 

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.

Other stays we love:

• Gorgeous Two Bedroom with Private Garden, Walk to Town 
• Luxury Home with Stunning Hudson River Views 

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.

Eat: Head to Communal Kitchen for locally sourced bites and great wine or find authentic homestyle Filipino eats at Karenderya.

• Distance from NYC: approximately 57 miles or 1 hours, 15 minutes by car 

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.

Other stays we love:

• Asbury Park Cottage 
• Asbury Park Beach Cottage 

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).

• Distance from NYC: approximately 85 miles or 2 hours by car 

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 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.

Other stays we love:

• Centrally Located Apt in Victorian Mansion 
• Pet-Friendly Apt in 1850's Victorian Mansion 

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.

• Distance from NYC: approximately 107 miles or 2 hour by car 

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. 

Other stays we love:

• Romantic Cottage with Hot Tub 
• Las Hideaway Family Home 

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: In Stroudsburg, we love Sweet Creams Cafe’s hearty sandwiches for lunch and Sarah Street Grill’s eclectic menu for dinner.

• Distance from NYC: approximately 68 miles or 1 hour, 30 minutes by car 

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.

Other stays we love:

• Downtown New Hope Victorian On The Canal 
• Elevated Two-Bedroom, Two-Bath Riverside Escape 

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.