Good for hippies at heart
2 hrs, 11mins by car

Though the name conjures a crowd splashed in tie-dye and the faint scent of marijuana, Woodstock isn’t actually where the 1969 festival was held. (That was in Bethel, about two hours away.) Even so, the town is a mix of retired hippies—a street there is named after the late great Band member Levon Helm—artists and city dwellers who feel the need to flee the metropolis on weekends. Woodstock the chance to connect with nature thanks to Overlook Mountain and its various trails as well as a healthy shopping scene with quaint local shops like Candlestock and the Golden Notebook and its weekend flea market, delicious food that can be found at places like Silvia and The Mud Cub and drinks at Station Bar & Curio.

Good for small town fans
1hr 20mins by Metro-North

This quaint city in Dutchess County boasts an exceptionally good eating, drinking and art scene for its size. Walk five minutes from the train station to Dia:Beacon, a modern art museum housed in a former Nabisco box factory. It houses the Dia Foundation’s permanent collection of works from the ‘60s on, including minimalist sculpture by Anne Truitt and Dan Flavin’s work with fluorescent lights. If you’d rather spend the day sampling some booze, Dennings Point Distillery on Main Street also offers tours and tastings of their bourbon, whiskey, gin and vodka every Friday and Saturday. Before you board the train back to the city, spend a few quiet minutes watching the sun set over the Hudson at Long Dock Park. — Annalise Mantz

Good for townies, thrifters and history buffs.
1 hr 50 mins by car

Once a sleepy town, the city of Kingston is experiencing a reawakening with more residents moving in these days. Dating back to the arrival of the Dutch in 1652, Kingston has a rich history as the state's first capital. During the Revolutionary War, it was burned by the British and in the 19th century, it became a transportation hub, situated right on the Hudson. Despite the fire, you can still see the gorgeous First Reformed Protestant Dutch Church of Kingston, which was organized in 1659, and many 17th century stone buildings, including the Senate House, which was built in the 1670s. The city is divided into different sections: Uptown, which includes the historic Stockade area; midtown, which is bisected by Broadway, the city’s main drag; and Rondout, near the creek and river, to the south, according to the New York Times. A handful of trendy stores and unique hangouts like Rough Draft, a bookstore and taproom, have opened recently as well as a number of restaurants slinging delicious food like Ship to Shore and Lola. The Ulster Performing Arts Center, inside a restored 1926 theater, regularly has events and the city is also home to a number of festivals, including the Kingston Jazz Festival and the Artists Soapbox Derby. The Trolley Museum of New York even offers 1.5-mile ride on weekends and holidays along the Rondout Creek waterfront to Kingston Point Park.

Good for hikers and nature enthusiasts
2 hrs by car

Picture this: over 8,000 acres of forests, cliffs, ponds and streams that are ideal for hiking, cycling, horseback riding, trail running, rock climbing and more. Just 90 miles north of New York City, in Ulster County, Mohonk Preserve is truly a nature lover's slice of paradise that, unlike most other hiking grounds, is also home to horseback riding opportunities within designated carriage roads that promise less foot traffic than other destinations. Make sure to start your day early to make a full day of it.

Good for those who want a mix of town and country
3hrs by LIRR or car

Beyond all the worth-the-trip views of riverside bluffs and verdant trees, New Paltz is the most historic on this list, with preserved houses that were around 100 years before we even became the U.S. of A. So, yeah. Pretty old. Learn about the lives of the 17th-century Huguenot settlers, as performers (dolled up in duds from the period) take you through 30 buildings over 10 acres, including seven historic homes and a reconstructed 1717 church. (Want to retain the back-to-basics spirit as you take in the National Historic Landmark District? Leave the selfie stick at home.)

Good for everyone
2 hrs 50mins by car

Tucked into the Catskills, this Ulster County hamlet is a real melting pot, the kind of place where you can expect to see a conservative old-timer and a Brooklyn lumbersexual sipping Buds along the bar in perfect harmony. For every no-nonsense staple (Phoenicia Diner), there’s a hipster newbie (the Graham & Co.). Try Peekamoose if you want to be trendy—the restaurant is known as the "Gramercy of the Catskills." If you’re looking to do something unique, float down the creek’s rapids—one of the most popular things to do in Phoenicia—or hike at Giant Ledge. The mellow, no-frills, hippie-dippie local culture makes it easy for anyone to relax here.

Good for photo enthusiasts
1hr by car

With its rolling green hills and massive sculpture installations, Storm King Art Center is tailor-made for stunning photographs. Art aficionados and nature lovers alike will enjoy wandering the 500-acre art park featuring works from more than 100 artists including Alexander Calder and Maya Lin. Take the guided tram tour around the park once to get the lay of the land, then set off on foot or rent a bike for a day of exploring and Instagramming. Visitors can even climb inside a select number of the works. The artistic flair extends to the riverfront village of Cornwall-on-Hudson, where you can dine at the eclectic restaurant–art gallery combo Painter’s. –Annalise Mantz

Good for hikers
2hrs by car

Between its rugged landscape and forested pine-barrens area, upstate has some stellar natural spots, and Minnewaska State Park Preserve is one of the best. The more than 22,000-acre spread has been converted into an egalitarian playground with 50 miles of trails, a new rock-climbing spot at the Dickie Barre cliffs, as well as old carriage roads well suited for mountain biking. Cool off with a swim in Lake Minnewaska or Lake Awosting, nestled between towering white bluffs and known for their translucent aquamarine color. Afterward, head to New Paltz for a break at the Water Street Market, where you can eat, shop, and take in art, outdoor movies on Monday nights (June–Aug) and free music on Tuesdays. Historic Huguenot Street is also worth a gander; the road features seven 300-year-old stone houses from the original settlement and provides a tangible glimpse at the history of the town. — Rosie Haney

Good for outdoorsy folk
70mins by Metro-North

The Hudson Highlands have lush landscapes, peaks and breathtaking hikes for all levels. Little Stony Point Loop offers a relaxed jaunt along a flat peninsula where you can wade into the Hudson River at the beach. Explore old ruins, including a crumbled mansion and defunct dairy farm, on the gradually sloping, partially unpaved Cornish Estate Trail, which starts opposite Little Stony Point Loop, marked by blue blazes. The adventurous should tackle the steep climbs and rock scrambles that lead to the summit of Breakneck Ridge for an impressive 360-degree vista of Storm King Mountain, Bannerman Castle and, on clear days, the Catskills. For detailed guidebooks and maps, check out New York–New Jersey Trail Conference, Open Space Institute and Appalachian Mountain Club, and bring water and appropriate footwear, even for the simpler treks. — Nadia Chaudhury

Good for history lovers
30–45mins by Metro-North to Tarrytown

Take a five-minute cab ride from the station to Philipsburg Manor Upper Mills living-history museum—a farm and mill dating back to 1750—to try hands-on activities. Staffers in period costume demonstrate grinding grain in the gristmill, threshing wheat and preparing goods for shipping with traditional instruments. The visit also provides a sobering reminder that slavery was not confined to the South, which guided tours highlight. Explore the dairy, kitchens and bed chambers in the main house, then bask in the rustic scenery from the bridge overlooking the pond. Take the 15-minute walk to the Bridge View Tavern for craft brews, pub grub, and views of the bridge and stretch of the Hudson River known as the Tappan Zee. —Lauren Piro

Good for pickers
1 hr 30 mins by car

A day at the orchard sounds nice, right? Warwick’s main attraction is Masker Fruit Farms—a 200-acre orchard open for apple picking seven days a week. Swing by the country store on your way out to pick up apple butter and a jug of cider and do a wine tasting at Demarest Hill Winery before a relaxing jaunt around the historic town.

Good for adventurers
4 hrs, 30 mins by car

Ithaca, on the southern tip of Cayuga Lake, is a college town through and through, but it's also got that rustic, upstate vibe and gorgeous fall foliage you're looking for with quaint Victorian homes to gaze at. It's a great getaway for those who want to go leaf-peeping and pumpkin picking but also want to check out the local town nightlife and its plethora of restaurants. The best part? It's near to some of New York's most incredible gorges and waterfalls. They don't say "Ithaca is gorges" for nothin'!

Good for history buffs
3 hrs by Amtrak

Washington, D.C. really isn't as far away as you might think and it's chock-full of fun things to do, from touristy visits of historical monuments to hikes in the great outdoors and more. Don't miss the National Gallery of Art or Meridian Hill Park for some incredible art and sculptures, respectively, and head to the lush Rock Creek Park around your scheduled visits to see the Capitol and the Lincoln Memorial. When thirsty, stop by Archipelago for some tiki drinks and feast at Union Market or Rose's Luxury. Check out our guide to all things D.C. here. — Shaye Weaver

Good for gamblers
1 hr 44mins by car

Take a walk on the wild side when you visit Bethlehem, Pennsylvania’s prime casino and resort: The Sands. Rattle the dice, try your luck on the slots, play table games or simply go for the cocktails. While there are ten fine dining options (including three Emeril’s eateries—bam!), we recommend hitting Main Street in historic Bethlehem for a bite. Enjoy a flight of sangria and eat small plates such as bacon-wrapped dates and, hummus ad burrata at Tapas On Main. Afterward, oblige your sweet tooth across the street at Penn State’s Creamy Ice Cream shop inside Hotel Bethlehem.

Good for culture hounds
1hr 30mins by Amtrak, 2hrs by bus

Skip southward to shop Philly’s flourishing secondhand scene of vintage clothing shops and thrifty treasure spots. A few steps off South Street (but still not far from a cheesesteak) is Heres2CoolStuff, acclaimed for its colorful and inexpensive collection of men's and women’s apparel. For dapper gentlemen, Briar boasts a meticulously edited collection of classic Americana style, including tailored sport coats, varsity jackets and military boots alongside sartorial accessories (bowties, cufflinks, hats) and oddities for the curious collector. Don’t leave without hitting up what just might be every Macklemore fan’s fantasy come true: Bulk Vintage, a warehouse for hunters who don’t mind digging—literally—for retro duds sold at wholesale prices that rival any thrift shop north of Jersey. If you can’t make the public opening hours, make an appointment to rummage. — Sammy Davis

Good for escape artists
45mins by car

Nudged up against the South Mountain Reservation, Greenwood Gardens (which opens May 1, 2021) presents a tranquil, isolated escape. The grounds have been around since the early 1900s, but not until April 2013, following several years of renovation, did they open to the public. Begin at the orientation center, a redbrick revival Georgian manor, and proceed to a formal Italianate garden marked by stone terraces and wooden pergolas. Follow stone paths to the rustic Arts and Crafts–style cottages, then wind your way to the three-foot-tall limestone chess pieces lining the steps to the teahouse. Seek out the summerhouse on your own and admire the resident swans, chickens and goats, or join a guide on a 45-minute walking tour. — Jen Michalski

Good for art aficianados
1hr 20mins by NJ Transit

Wandering amid the 270 pieces of contemporary art at Grounds for Sculpture, five minutes by cab from the Hamilton station, makes for a serene escape, with playful surprises around every corner. Visitors are encouraged to snoop for secret spots among the 42 picturesque acres, such as the hidden hammock room near the Nine Muses sculpture (take a snooze without fear—the door locks from the inside), and keep an eye out for the many peacocks. The park’s indoor gallery at Seward Johnson has four exhibits, including two site-specific glass installations by sculptor Daniel Clayman. End your day with upscale local cuisine at on-site restaurant Rat’s. Nibble on the mussels mouclade and the charcuterie platter, or sip a cocktail during happy hour. Imbibe on the patio overlooking a re-creation of Monet’s iconically depicted bridge in Giverny, or even bring your drink out into the park. — Lauren Piro

Good for bicyclists
30min by bike

Throw on your best Lululemon gear and head to the next state over for a cycling jaunt. If you don’t have your own set of wheels, stop by Tread Bike Shop; rentals include helmets, and the friendly staff supplies sage advice for newbies. Set off and make your way through the hilly, neighborhood streets of Inwood and follow signs for the George Washington Bridge. Take in panoramic views of Manhattan while gliding over the Hudson via the bridge’s cyclist-and-pedestrian-only path. Veer left to stay on Henry Hudson Drive, the Palisades’ main bike path, which will take you along mountain roads past rustling trees and views of the water. At the bottom of the trail, riders will find grassy picnic areas on the river. The return ride back to the city is, mercifully, a simpler, mostly downhill ride. — Allison Merzel

Good for architecture fans
1hr 15mins by Metro-North

Architect Philip Johnson built a completely transparent modern home on his 47-acre estate in Connecticut in 1949, a feat that quickly brought him worldwide notoriety. You might also recognize his work from the sculpture garden at MoMA. After his death, the Glass House was opened to the public in 2007. Curious visitors can explore the property by buying a timed ticket to for the one-hour, two-hour or three-hour tour. Take in the sleek, spartan design, then head into town to spy some examples of classic New England architecture. There’s the one-room Little Red Schoolhouse, the Greek Revival Hanford-Silliman House and a replica of the original Cody Drug Store from 1918. Stop for a freshly made dulce de leche gelato at Gelatissimo before leaving town. — Annalise Mantz

Good for wanderers
2 hrs by car

Located in southwest Connecticut, Silvermine isn't a far trek from NYC, but it offers enough of an escape to be a perfect getaway. The historic town, dating back to the late 1600s, has largely centered around Silvermine Tavern, a historic mill that still hosts jazz weekends and wine dinners. The Silvermine River runs through the heart of the village. Stop at The Silvermine Arts Center and wander Grace Farms, an 80-acre public nature preserve with a giant, prize-winning, river-inspired building designed by a Japanese firm. If you want more architecture, visit the modern and aptly named Philip Johnson Glass House.