The Roundup

How to Have Fun Outside in New York and Beyond - Fall 2021

by Team Fathom
Upstate A fall day in upstate New York. Photo by Andrew S/Unsplash.

New York is resilient in countless ways. We turned our asphalt into pedestrian zones, dining huts, dance floors, parade routes, and cycling lanes. Hudson Valley expanded its farmers markets so that more people could grocery shop in the fresh air. North Fork movie theaters reimagined their drive-ins for nightly screenings under the stars. The Hamptons took its art — and wine — outside for sculpture exhibitions and vineyard tastings.

And while we're not as mask-free as we had hoped to be, we all know that being outside (or inside with a wide-open window) is the best way to pass the time. As fall ushers in and temperatures drop, we hope you'll consult this list to continue having more fun outdoors in Greater New York.

Photo by Florian Wehde/Unsplash.

New York City

If You're in the Mood For: Long strolls in Central Park, al-fresco sidewalk dining, leaf-peeping on charming brownstone-filled blocks, lining up for a brewery crawl, and making up your own food tours.

Lay of the Land: If you don't have your NYC bearings, it's good to know that the city is made up of five large boroughs at the corner of Hudson River and Atlantic Ocean. In the most general of terms: action-packed Brooklyn and Manhattan are separated by the East River; the food and culture mecca known as Queens is north and east of Brooklyn; Staten Island is a skip from Coney Island and south Brooklyn; the Bronx is north of Harlem. There are a lot of people around here — some eight million. The best way to keep your distance while still feeling all the energy is to walk, walk, walk the streets. (And always look where you're going.)

Your Agenda: It's impossible to leave Yayoi Kusama's KUSAMA: Cosmic Nature exhibition at the New York Botanical Garden in the Bronx without a smile. The nonagenarian Japanese artist's iconic polka dot explosions wrap tall trees, while her oversize fiberglass flowers fill the glass observatory. When you get your fill of peaceful, playful nature, head over to Arthur Avenue for a fun Italian-American dining adventure checking out old-school pastry shops, import shops, taverns, pubs, and pizza parlors. Or spend a day sampling the city's slices with Scott's Pizza Tours, where a pie-obsessed guide takes you for a slice in each borough. Culinary Backstreets heads to the off-beat neighborhoods in Queens and beyond for in-depth introductions to hidden hole-in-the-walls and some of the best meals you'll ever have. If you'd rather not eat on the go, but still want to stumble upon cool places, hop on a Citi Bike and check out these beginner biking routes to explore each borough.

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Charming Rowland House, one of the Inns of Aurora. Photo courtesy of Finger Lakes Regional Tourism Council.

Finger Lakes

If You're in the Mood For: Lakeside vineyards, beautiful rolling hillside farms, nature preserves, and waterfalls.

Lay of the Land: The lakes form a triangle of sorts (they really do look like fingers!), bordered by the big towns of Rochester to the northwest, Syracuse in the northeast, and Ithaca in the south. The towns and lakes to focus on are Ithaca and Aurora on Cayuga Lake and Geneva on Seneca Lake.

Your Agenda: The nicest places to stay in the Finger Lakes are centuries-old manors that have been beautifully restored and converted into inns, like Argos Inn and The William Henry Miller Inn in Ithaca and the lakeside beauty that is Inns of Aurora in Aurora. In Ithaca, grab breakfast at Carriage House Cafe or, if you’re visiting on weekends (until October), the historic Ithaca Farmer's Market at the Cayuga Lake inlet has great grab-and-go pastries. For dinner, Mercato serves delicious Italian-inspired, seasonal cuisine with a terrific Italian wine list — and al-fresco seating. If you want to add some cardio to your drinking and dining, hit the Canandaigua Lake Wine Trail, with a collection of wineries, breweries, and food trucks found along a scenic trail above Canandaigua Lake. Taughannock Falls State Park has one of the highest waterfalls east of the Rockies, which makes a nice pairing with a peaceful beach walk at Cayuga Lake.

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Photo courtesy of Urban Cowboy Lodge.

Hudson Valley

If You're in the Mood For: Leafy drives, local wineries and breweries, mountain views, and a burgeoning food and farmer's market scene.

Lay of the Land: The Hudson Valley extends 150 miles above the tip of Manhattan and has long been a destination for city dwellers to explore the countryside.

Your Agenda: Go apple picking at Fix Bros Fruit Farm. Pick up a six pack of house brews from Woodstock Brewing on Route 28 (next to Phoenicia diner) and picnic near the river. Leaf peep at Overlook Mountain, a 4.6 mile loop with 360-degree views; Opus 40, the six-acre outdoor earthwork sculpture garden in Woodstock; or Tannersville's Mountain Top Arboretum, which has 178 acres of trails, wetlands, gardens, and native plants to roam and explore. And once all that fresh air has triggered your appetite, grab a seat on the open-air deck at Silvia on the main strip in Woodstock for elevated plates of locally sourced veggies and organic meat provided from over twenty local farms. At sundown, retreat to a rustic-chic room at Urban Cowboy Lodge with Pendleton textiles, copper claw-foot tubs overlooking the mountains, potbelly stoves, and a seriously cool bar with equally cool bartenders to get the local rundown. And for the ultimate forest-bathing experience, book a private A-frame cabin at Eastwind nestled on a quaint hillside in Windham where you'll fall asleep to a starry-night canopy and spend the cozy mornings with a great book and canteen of hot brew.

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Photo courtesy of Grace Farms.

New York-Connecticut Border

If You're in the Mood For: Taking in art at a leisurely pace, bucolic private estates, eating a fine meal surrounded by antiques, and daydreaming about living a peaceful, catered-to countryside existence.

Lay of the Land: Dutchess County is just two easy hours from New York City on the border of Litchfield County, Connecticut. It's a great place to be outdoors no matter the season with hiking, biking, snowshoeing, and cross-country skiing easily accessible.

Your agenda: From May to November you can visit the striking see-through glass home designed by Philip Johnson in the 1940s, The Glass House is open for tours that include a peep at his painting and sculpture galleries and the outdoor one-mile walk over grassy pathways with unique vantages of the house. Design junkies with small children (who need a less fragile art experience) can get their fix at nearby Grace Farms, a fascinating non-profit center on 80 acres of fields and woods with a curvaceous structure built of steel, concrete, wood, and glass that meanders through the landscape and brings the outdoors in. There's also a peaceful library, a bright cafe and tea pavilion, a craft center, and a gymnasium to tire the kiddos out. Once your appetite shifts from art to food, head to the small print shop, bar, and pizzeria called The Lantern, where the pies are created by an alumnus of Brooklyn’s beloved Roberta’s. The venue also hosts live music events and pop-up Sunday brunches. And if you're not ready to head back to the city life, book a room at Troutbeck, a 250 year-old inn and gathering spot in Amenia, where you're swept up in the history of the place from the approach: a glorious lawn leading to a massive slate-covered Manor House.

Stay Outside:
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Photo by Daniel Schwartz.

North Fork

If You're in the Mood For: Old-fashioned farming villages and seaports, nautical decor that feels collected — not cliché — and a slice of seaside living that is high on charm and low on formality.

Lay of the land: The 30-mile-long peninsula has a long history of agricultural industries, including apple orchards, potato and sod farms, and vineyards.

Your Agenda: Embrace the great outdoors at Hallockville State Park Preserve, a relatively new shorefront park with nearly one mile of pristine beachfront on the north shore of Long Island, plus 225 acres of woodland between Riverhead and Southold. Take an hour to walk a well-maintained trail, observe migrating birds, or let the kids roam in the fields. Cap off the al-fresco day with farm-to-table Italian fare at Barba Bianca, a chic evening-only restaurant with dockside seating or throw one back at Little Creek Oyster Farm & Market, a quaint seaside oyster stand and bar overlooking Greenport Harbor. It's an easy sell to extend the weekend when you post up at Sound View, a next-generation motel with design cred and stellar seaside views. On your way out of town, brighten your day (or someone else's) at Morning Sun Shop with gifts of locally made sea salt, cider, tea, and ceramics, as well as beautiful produce. It's also essential to swing by North Fork Food Truck for a lobster roll from the folks behind The North Fork Table & Inn (the grand dame of the Long Island wine country culinary scene) and don't forget a pie at Briermere Farms.

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Photo courtesy of Shou Sugi Ban House.


If You're in the Mood For: Long (crowd-free) beach walks, apple picking, lobster rolls (who said you can only eat them four months of the year?), renting a sailboat, or finally taking that surf lesson.

Lay of the Land: The Hamptons is comprised of a series of villages and hamlets that stretch along Long Island's South Fork. The strip of coastline has long been a refuge for New York City's elite who can escape Manhattan’s dense urban jungle to for quiet seaside homes (cough, mansions), al-fresco romantic dinners, surf spots, and clam-bakes. And while each summer Highway 27 fills up for miles with cars racing to their chic weekend agendas, the fall has increasingly become a not-so-secret secret off season as the crowds dissipate, the ocean's warm, and you can get from Hampton to Hampton without sitting in hours of traffic.

Your agenda: Without the exclusive parties and sunset concerts, fall in the Hamptons can be a relaxing time to unwind and take care of yourself. Especially at Shou Sugi Ban House in Watermill, where the grounds are open and airy with beautiful landscaping, outdoor spa pools, and the retreat's agenda is focused on health and wellbeing. Or you can surround yourself with wildlife at Elizabeth A Morton National Wildlife Refuge in Sag Harbor, a serene wooded bluff overlooking the bays that are home to long-tailed duck, piping plover, painted turtles, osprey, and other elegant sea birds who peck among the salt marsh, rocky beach, and lagoon. Parrish Art Museum, a beautifully minimalist space in Water Mill, hosts short film screenings, evening art projections, and painting en plein air on Friday mornings. Fall is harvest season for the bounty of vineyards on the South Fork, like the Innovative, sustainable, small-batch grape growers at Channing Daughters with an experimental vineyard block, and planted sculpture-and-tasting garden.

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We make every effort to ensure the information in our articles is accurate at the time of publication. But the world moves fast, and even we double-check important details before hitting the road.