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Getaways from New York · Winter 2026–27

Winter getaways from New York

Seventeen ways out of New York between December and March, from an 80-minute train to Dia Beacon to a two-hour flight to Bermuda. Each is sorted by how you get there, with the event worth timing it for, where to stay and one thing to know before you go.

  • 17trips
  • 8by car
  • 7by train
  • 2by air
  • Facts checked 21 October 2026

17 winter trips from New York, sorted by how you get there: 8 by car, 7 by train and 2 by air. The quickest to reach is Philadelphia, 1 hr 11 min away; the longest trip is Stowe, 6 hr 30 min. Each one lists the travel time, the dates worth timing it for and where to stay.

At a glance

GetawayFrom New YorkBest forTime it for
Mohonk & the Shawangunks 1 hr 30 min Spa, Romantic, Family Winter Family Fun at Mohonk, 15–18 Jan 2027
Hunter & the Catskills 2 hr 30 min Ski, Family, Outdoors January and February, once both mountains are fully open
The Berkshires 2 hr 30 min Spa, Culture, Outdoors January to March, when the Clark has offered free admission in recent winters and Notchview's ski trails are open
Cape May 3 hr Romantic, Festival, Family Christmas Candlelight House Tour, 5–19 Dec 2026
Newport 3 hr Romantic, Culture, Festival Holidays at the Newport Mansions, 21 Nov 2026 – 3 Jan 2027
Woodstock, Vermont 4 hr 30 min Romantic, Ski, Festival Wassail Weekend, 11–13 Dec 2026
Lake Placid & the Adirondacks 5 hr Ski, Outdoors, Family FIS Ski Jumping and Nordic Combined World Cups, 5–7 Feb 2027
Stowe 6 hr 30 min Ski, Romantic, Festival Stowe Winter Carnival (2027 dates TBA)
Philadelphia 1 hr 11 min City break, Culture, Festival PHS Philadelphia Flower Show, 13–21 Mar 2027
Beacon & Dia Beacon 1 hr 20 min Culture, Romantic, Outdoors Any Friday to Monday from December to February, when Dia Beacon keeps winter hours of 10 a
Hudson & Olana 2 hr Culture, Romantic, Outdoors Any weekend from December to March
Washington, DC 2 hr 57 min City break, Culture, Festival National Cherry Blossom Festival, 20 Mar – 11 Apr 2027
Providence 3 hr 5 min City break, Food & wine, Culture December, for WaterFire's holiday lightings, or January to early March while the downtown rink is open
Montauk 3 hr 8 min Spa, Outdoors, Romantic Montauk Point seal hikes, 5–20 Dec 2026
Boston 3 hr 54 min City break, Festival, Culture Boston Frostival, 22 Jan – 5 Mar 2027
Montréal Passport 1 hr 30 min City break, Festival, Food & wine Montréal en Lumière, 18–28 Feb 2027
Bermuda Passport 2 hr 5 min Romantic, Food & wine, Spa Bermuda Restaurant Weeks (2027 dates TBA)

By car 8 trips

1 hr 30 min
Photograph · Mohonk Mountain House
Hudson Valley, New York, USA

Mohonk & the Shawangunks

About 90 minutes by car; Wildflower Farms puts Gardiner "just 90 minutes from New York City" and Mohonk is about 90 miles northMetro-North or Amtrak to Poughkeepsie, then taxi; or Adirondack Trailways from Port Authority to New Paltz, where Mohonk will collect guests with 24 hours' notice.

Three of the region's most complete winter retreats sit within the Shawangunk Ridge country: Mohonk Mountain House, set in 40,000 acres of protected forest with skating and snow tubing, and the newer Wildflower Farms and Inness. All are about 90 minutes from Manhattan, close enough for a Friday-night arrival.

Time it for Winter Family Fun at Mohonk 15–18 Jan 2027

Mohonk's signature family weekend with kids' club sessions, snow tubing, open-air skating and daily themed performances.

Do
  • Winter at Mohonk "Every winter, the lake freezes over"; the resort lists ice skating on an outdoor rink, snow tubing, guided hikes and daily fitness classes.
  • Thistle, Wellbeing by Auberge The spa at Wildflower Farms, on 140 acres facing the Shawangunk Ridge in Gardiner.
Stay
  • Mohonk Mountain House Established in 1869 and "nestled in 40,000 acres of protected forest"; overnight rates include dining from dinner on arrival to lunch or brunch on departure.
  • Wildflower Farms, Auberge Collection 65 accommodations including free-standing cabins on 140 acres in Gardiner, with views of the Shawangunk Ridge and the Thistle spa.
  • Inness 28 private cabins and 12 Farmhouse rooms in Accord, with dining, spa and golf on site.

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Winter tip Mohonk's rates include most meals, so compare them against Wildflower Farms or Inness on a total-trip basis rather than room rate alone.

2 hr 30 min
Photograph · Hunter Mountain
Catskills, New York, USA

Hunter & the Catskills

About 2 hr 30 min by car via the New York State Thruway (I-87), per Hunter MountainAmtrak to Hudson (about 2 hours from Moynihan Train Hall), then about 40 minutes by taxi to Scribner's; Adirondack Trailways runs daily from Port Authority.

Two Catskills ski mountains sit about two and a half hours up the Thruway: Hunter, with 1,600 feet of vertical, and state-run Belleayre, with a gondola and 62 trails. Scribner's gives the trip a design-led base with a year-round pool and hot tub.

Do
  • Hunter Mountain 1,600 feet of vertical, a dedicated learning area (Hunter One) and a 1,000-foot tubing hill; on the Epic Pass.
  • Belleayre Mountain 3,429-foot summit, 1,404 feet of vertical, 62 trails on 171 acres, 96% snowmaking and the Catskill Thunder Gondola.
Stay
  • Scribner's Catskill Lodge "A design-forward mountain lodge in Hunter" with rooms, cabins and bungalows, Prospect restaurant and a year-round pool and hot tub.

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Winter tip Hunter is on Vail's Epic Pass, and Vail says pass holders get 20% off food, lodging and group lessons, so price a Northeast Value or Midweek pass before buying day tickets for a two-day trip.

2 hr 30 min
Photograph · BenFrantzDale / Wikimedia Commons (CC BY-SA 2.5)
Western Massachusetts, USA

The Berkshires

About 2 hr 30 min by car (about 140 miles), per the Berkshires visitors bureauThe visitors bureau says a car is strongly recommended and ride share is limited in the region.

The Berkshires pair two destination wellness resorts in Lenox, Canyon Ranch and Miraval, with serious art at the Clark and 25 miles of Nordic trails at Notchview. It is two and a half hours from the city and quiet between the summer festivals.

Do
  • Clark Art Institute, Williamstown Open 10 a.m. to 5 p.m., Tuesday to Sunday, September to June; admission was free for all from January to March 2026 under its "Free for Three" program, and the grounds are always free.
  • Notchview, Windsor The Trustees' 3,108-acre reservation, mostly above 2,000 feet, with 25 miles of ski trails (5 groomed for skate skiing), open early December to early April, conditions permitting.
Stay
  • Canyon Ranch Lenox All-inclusive wellness resort around the Bellefontaine Mansion, with unlimited meals and 35-plus optional daily activities.
  • Miraval Berkshires Resort & Spa 380 acres in Lenox designed by Frederick Law Olmsted, centred on the 1894 Wyndhurst Mansion.

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Winter tip The Clark's free winter admission is described as an ongoing program now in its fourth year, but 2027 has not been confirmed; check before building a trip around it.

3 hr
Photograph · Cape Resorts / Congress Hall
New Jersey, USA

Cape May

About 2 hr 30 min to 3 hr 30 min by car via the Garden State Parkway to Exit 0, per Congress Hall

Cape May's Victorian historic district turns December into its second season, with candlelit house tours and trolley rides run by the local Cape May MAC. Congress Hall's lawn becomes a holiday village with a carousel and a train.

Time it for Christmas Candlelight House Tour 5–19 Dec 2026

Self-guided evening tour of decorated homes, inns, churches and hotels in the historic district, with an express shuttle; dinner packages on 12 and 19 December.

Do
  • Congress Hall Winter Wonderland Carousel and Congress Hall Express train rides, a vendor village and seasonal food and drink, Thursday to Sunday from 27 November to 31 December 2026; tree lighting on 4 December.
  • Lamplighter Christmas Walking Tour Cape May MAC's evening walking tour of decorated Victorian inns, 5:30 to 7:30 p.m.
Stay
  • Congress Hall Billed as "America's Oldest Seaside Hotel," with its own holiday village on the Grand Lawn through December.

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Winter tip Cape May MAC recommends buying Candlelight House Tour tickets in advance; wristbands and maps are collected at the Physick Estate the day before or the day of the tour.

3 hr
Photograph · The Preservation Society of Newport County
Rhode Island, USA

Newport

About 3 hours (175 miles) by car, per Discover NewportAmtrak to Providence (about 3 hr 5 min by Acela), then about 30 minutes by road, or to Kingston, where RIPTA bus 64 runs to downtown Newport except on Sundays and holidays.

The Preservation Society dresses The Breakers, Marble House and Chateau-sur-Mer for the holidays with nearly 30 themed trees, and on select evenings The Breakers' grounds glow with Sparkling Lights. Castle Hill Inn and The Chanler make it a winter weekend on the water.

Time it for Holidays at the Newport Mansions 21 Nov 2026 – 3 Jan 2027

The Breakers and Marble House open daily and Chateau-sur-Mer on weekends, all decorated for the season.

Do
  • Holidays at the Newport Mansions Nearly 30 decorated trees across three houses, including a 15-foot poinsettia tree of 150 plants in The Breakers' Great Hall; The Breakers needs a timed ticket.
  • Sparkling Lights at The Breakers A half-mile path of holiday lights plus the decorated interior, on select evenings 21 November to 27 December 2026, 4 to 8 p.m.; adults $45.
Stay
  • Castle Hill Inn On a 40-acre peninsula where Narragansett Bay meets the Atlantic, a year-round retreat since it was winterized after the war; Rhode Island's first Relais & Châteaux member (2008).
  • The Chanler at Cliff Walk Individually designed rooms and villas on the Cliff Walk, themed from Regency to Moroccan, with the Cara restaurant.

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Winter tip Sparkling Lights entries run every half hour from 4 to 6 p.m. on a separate timed ticket that also covers The Breakers' interior, so it can replace a daytime visit.

4 hr 30 min
Photograph · Woodstock Inn & Resort
Vermont, USA

Woodstock, Vermont

About 4 to 4 hr 30 min by car, per the Woodstock Area Chamber of Commerce; the Woodstock Inn puts it 263 miles from New York CityNearest airports are Lebanon, NH, Burlington and Boston Logan, per the chamber.

Woodstock's Wassail Weekend brings a horse parade, luminaries on the green and a Yule log bonfire. After the holidays, the Woodstock Inn's own ski hill and Nordic centre, and Twin Farms nearby in Barnard, carry the season.

Time it for Wassail Weekend 11–13 Dec 2026

The 42nd Wassail Weekend: artisan market on the green, a Yule log bonfire and luminaries on 12 December, and horse and carriage rides through the village.

Do
  • Saskadena Six The Woodstock Inn's ski area, in operation since 1936, with Perley's Pourhouse slopeside.
  • Woodstock Nordic Center The inn's cross-country ski centre with what it calls an extensive trail network, plus snowshoeing near the inn.
  • Billings Farm & Museum Winter Celebration Victorian-themed celebration with holiday lights and family activities, 11 to 13 December 2026, during Wassail Weekend.
Stay
  • Woodstock Inn & Resort 142 rooms and suites, with a LEED-certified spa, the Red Rooster restaurant, Saskadena Six and the Nordic centre.
  • Twin Farms All-inclusive retreat in Barnard for adults (14 and over), with meals, drinks, on-site skiing, snowshoeing and sledding included.

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Winter tip Wassail Weekend's welcome party at Peace Field Farm on 11 December is ticketed with limited availability, so book it with the room.

5 hr
Photograph · Cody Updike / Lake Placid ROOST
Adirondacks, New York, USA

Lake Placid & the Adirondacks

About 5 hours (288 miles) by car, per Lake Placid ROOSTCape Air flies from JFK to Adirondack Regional Airport (SLK), about 20 minutes from Lake Placid; Amtrak's daily Adirondack reaches Westport in about 6 hr 20 min; Adirondack Trailways runs from Port Authority.

The two-time Olympic host lets visitors use its venues: skate the outdoor Olympic oval, ride the sliding track head first, and ski Whiteface's 3,430 feet of vertical. In February the World Cup returns to the ski jumps.

Time it for FIS Ski Jumping and Nordic Combined World Cups 5–7 Feb 2027

Three days of World Cup ski jumping and Nordic combined at the Olympic Jumping Complex.

Do
  • James C. Sheffield Speed Skating Oval Public skating on the outdoor Olympic oval through the season; adults $15, with rentals.
  • Skeleton Experience, Mt Van Hoevenberg A solo, head-first run down the Olympic sliding track at 30 mph, $75; the venue also grooms 55 km of cross-country trails (5 km with snowmaking).
  • Whiteface Mountain 3,430 feet of vertical (billed as the most in the East), 95 trails, more than 299 skiable acres and 99% snowmaking.
Stay
  • Mirror Lake Inn Resort and Spa Lakefront resort holding AAA Four-Diamond status for more than three decades, with a spa, heated indoor and outdoor pools, a seasonal rink on the lake and free snowshoes.

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Winter tip The World Cup weekend ends on 7 February, a week before NYC's Midwinter Recess (15 to 19 February); families on the recess week should book Whiteface lessons early instead.

6 hr 30 min
Photograph · Mark Vandenberg / Go Stowe
Vermont, USA

Stowe

About 6 hr 30 min by car, per Go StoweDelta flies nonstop from JFK and LaGuardia and United from Newark to Burlington (BTV), which Stowe says is a 40-minute drive; Amtrak's Waterbury station is 17 miles from the resort.

Stowe pairs Mt. Mansfield's 116 trails with Spruce Peak's ski-in, ski-out village, linked by the Over Easy Gondola. Fly to Burlington to cut the drive to under an hour from the gate.

Time it for Stowe Winter Carnival 2027 dates still to be announced; ran in January 2026

Village festival built around professional ice carving.

Do
  • Stowe Mountain Resort Mt. Mansfield rises to 4,395 feet, with 485 skiable acres, 116 trails and 12 lifts; the Over Easy Gondola links Mt. Mansfield and Spruce Peak.
  • Stowe Winter Carnival ice carving Professional carvers work through the village on a demonstration day and a competition day.
Stay
  • The Lodge at Spruce Peak Billed as "Stowe's only ski-in, ski-out luxury resort," with suites up to three bedrooms and the Spa at Spruce Peak.

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Winter tip Burlington's New York nonstops are listed as year-round by the airport, which turns a 6.5-hour drive into a short flight plus about 40 minutes on the interstate.

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By train 7 trips

1 hr 11 min
Photograph · Delaware River Waterfront Corporation
Pennsylvania, USA

Philadelphia

About 1 hr 10 min by Amtrak Acela, Moynihan Train Hall to Philadelphia 30th Street (Amtrak timetable)Amtrak's weekday Acela departures at 1:02 p.m. and 2:37 p.m. each reach Philadelphia in 70 to 71 minutes; the Saturday and Sunday 10:03 a.m. takes 76.

At just over an hour by Acela, Philadelphia is the shortest rail trip on this list, and its winter calendar ends on a high: the PHS Philadelphia Flower Show fills the Convention Center for nine days in mid-March. Before that, the Barnes collection and a riverfront rink under the Ben Franklin Bridge carry a weekend.

Time it for PHS Philadelphia Flower Show 13–21 Mar 2027

The Pennsylvania Horticultural Society's show, now in its 198th year, at the Pennsylvania Convention Center; the 2027 theme is ICONIC, "a bold celebration of the garden as muse."

Do
  • The Barnes Foundation Open Thursday to Monday, 11 a.m. to 5 p.m.; the $30 adult ticket includes the special exhibition and is valid for two consecutive days.
  • Independence Blue Cross RiverRink Winterfest Skating, cabins and firepits on the Delaware River waterfront with the Ben Franklin Bridge as a backdrop, open 27 November 2026 to Sunday 28 February 2027.
Stay
  • The Rittenhouse On Rittenhouse Square, with suites of 650 to 2,000 square feet, an atrium pool and spa, Lacroix and live jazz in The Library bar.
  • Four Seasons Hotel Philadelphia at Comcast Center 227 rooms on the top 12 floors of Norman Foster's 60-storey tower, with Jean-Georges on the 59th floor and an infinity-edge indoor pool on the 57th.

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Winter tip Flower Show weekends are the busiest; the show runs Saturday 13 to Sunday 21 March 2027, so a midweek visit inside that window is easier on both tickets and the Acela.

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1 hr 20 min
Photograph · Acroterion / Wikimedia Commons (CC BY-SA 4.0)
Hudson Valley, New York, USA

Beacon & Dia Beacon

About 80 minutes by Metro-North Hudson Line from Grand Central, per the MTADia Beacon is an 8 to 10 minute walk from Beacon station, and the Beacon Free Loop bus runs Monday to Saturday between the station and the museum (MTA). For Hudson further north, Amtrak's Empire Service takes about 2 hours from Moynihan Train Hall.

Dia Beacon's collection, from the 1960s to the present, fills a former Nabisco box-printing factory on the Hudson, and in winter the galleries are at their quietest. It is the easiest car-free day or overnight from Manhattan: the train runs up the river and the museum is a short walk from the platform.

Do
  • Dia Beacon Dia's collection in a former Nabisco box-printing factory at 3 Beekman Street, open Friday to Monday 10 a.m. to 4 p.m.; general admission $25.
  • Weekend public tours Free with admission every Saturday and Sunday at 12 p.m. and 1:30 p.m.
Stay
  • The Roundhouse Set directly on Fishkill Creek steps from Main Street, with creek and waterfall views from several rooms and its own restaurant and lounge.

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Winter tip Dia Beacon is closed Tuesday to Thursday and on Christmas Eve, Christmas Day and New Year's Day, so plan a Friday-to-Monday trip and avoid 24 and 25 December and 1 January.

2 hr
Photograph · Netniks / Wikimedia Commons (CC BY-SA 4.0)
Hudson Valley, New York, USA

Hudson & Olana

About 2 hours by Amtrak Empire Service, Moynihan Train Hall to Hudson (Amtrak timetable)Daily Empire Service trains at 11:20 a.m. and 4:45 p.m. take 2 hr 2 min and 1 hr 58 min; the daily Adirondack (8:15 a.m.) takes about 2 hr 10 min. By car, Olana puts itself about 2.5 hours from New York City.

Two hours up the river by Amtrak, Hudson pairs Warren Street, home to The Maker hotel and the Hudson Opera House, with Frederic Church's Olana just outside town. Olana's park stays open every day of the year and is free, with a self-guided audio tour of the landscape Church designed.

Do
  • Olana State Historic Site Home of Hudson River School painter Frederic Edwin Church; the park is open daily 8 a.m. to sunset and free, with a free self-guided landscape audio tour. Historic House tour hours vary by season and winter times were not posted as of 21 Oct 2026.
  • Hudson River Skywalk Olana recommends the Skywalk across the river to the Thomas Cole National Historic Site.
  • Hudson Hall Performing arts venue in the historic Hudson Opera House at 327 Warren Street.
Stay
  • The Maker 11 rooms across three historic buildings on Warren Street, including studios in a Georgian mansion themed for the Architect, Artist, Writer and Gardener, with a restaurant, café, lounge, courtyard garden and pool.

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Winter tip Hudson's Winter Walk on Warren Street no longer runs: Hudson Hall stepped down from producing it in 2024, so check Hudson Hall's December calendar for its smaller holiday events instead.

2 hr 57 min
Photograph · Destination DC
District of Columbia, USA

Washington, DC

About 3 hours by Amtrak Acela, Moynihan Train Hall to Washington Union Station (Amtrak timetable)Weekday Acela trains at 1:02 p.m. and 2:37 p.m. take 2 hr 57 min and 3 hr; the weekend 10:03 a.m. takes about 3 hr 28 min.

Washington's free Smithsonian museums carry a winter weekend, and the Acela makes it a three-hour, city-centre-to-city-centre trip. Stay into late March and the National Cherry Blossom Festival opens on 20 March 2027.

Time it for National Cherry Blossom Festival 20 Mar – 11 Apr 2027

Opening ceremony on 20 March at DAR Constitution Hall and the Blossom Kite Festival on the Washington Monument grounds on 27 March.

Do
  • Free museums on the Mall Destination DC lists the Smithsonian museums among the city's free attractions; the National Zoo is free but needs passes.
  • National Gallery of Art Sculpture Garden Ice Rink Rink among the garden's sculptures on the National Mall; last season ran 24 November 2025 to 1 March 2026 at $15 for ages 13 and up, and 2026-27 dates were not posted as of 20 Oct 2026.
Stay
  • The Jefferson Billed as "an independent, iconic landmark in the nation's capital" near the White House, with Quill bar and The Greenhouse.
  • Rosewood Washington, D.C. On the C&O Canal in Georgetown since 2013 (Rosewood since 2016), with a rooftop indoor-outdoor pool, CUT DC and the CUT Above rooftop bar.

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Winter tip Cherry blossom peak bloom moves every year and the Park Service only forecasts it closer to spring, so book refundable rates for late March and decide once the forecast is out.

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3 hr 5 min
Photograph · Providence Warwick CVB (GoProvidence)
Rhode Island, USA

Providence

About 3 hr 5 min by Amtrak Acela, Moynihan Train Hall to Providence (Amtrak timetable)Weekday Acela departures at 11:40 a.m., 2:01 p.m. and 6:05 p.m. reach Providence in 3 hr 5 min to 3 hr 10 min. Newport is about 30 minutes by road from Providence, per Discover Newport.

Providence is three hours by Acela and walkable from the station, with a winter program that runs skating and ice bumper cars downtown and two weeks of Restaurant Weeks specials. WaterFire, usually a May-to-November event, lights the basin for the holidays in December.

Do
  • The Providence Rink Downtown rink with public skating and ice bumper cars; last season opened 23 December 2024 and ran to early March, weather permitting. 2026-27 dates were not posted as of 21 Oct 2026.
  • WaterFire holiday events Go Providence lists a Holiday Basin Lighting on 11 December and a New Year's Eve event on the Michael S. Van Leesten Memorial Bridge on 31 December; the main fire installation of nearly 100 bonfires runs May to November.
  • Providence Restaurant Weeks Two weeks of dining specials in winter, per Go Providence; 2027 dates not listed.
Stay
  • The Beatrice 47-room hotel at 90 Westminster Street in downtown's historic district, with Bellini Providence and Bellini Rooftop.

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Winter tip Combine Providence with Newport: the Acela gets you to Providence in about three hours and Newport's holiday mansions are about 30 minutes further by road.

3 hr 8 min
Photograph · Discover Long Island
Long Island, New York, USA

Montauk

About 3 hr 10 min by LIRR from Penn Station on the direct weekend morning trains (LIRR Montauk Branch timetable)LIRR's Saturday and Sunday 7:47 a.m. from Penn Station reaches Montauk at 10:55 a.m.; the weekday 11:09 a.m. arrives at 2:26 p.m. Times are from the autumn timetable (to 8 November 2026); check the winter timetable before booking.

Off season, Montauk trades crowds for seals: New York State Parks runs guided hikes to a haul-out spot at Montauk Point in December, and the park stays open year-round for snowshoeing and cross-country skiing. Gurney's heated indoor seawater pool looks straight at the Atlantic.

Time it for Montauk Point seal hikes 5–20 Dec 2026

New York State Parks' guided winter hikes to the seal haul-out at Montauk Point.

Do
  • Seal hikes, Montauk Point State Park A 3-mile there-and-back hike to a seal haul-out spot, scheduled for 5 and 20 December 2026.
  • Montauk Point State Park Open year-round, sunrise to sunset, with trails for hiking, snowshoeing and cross-country skiing beside a lighthouse the park calls the oldest in New York State, commissioned in 1792.
  • Gurney's Seawater Spa A 30,000-square-foot spa with seawater and marine-based therapies; the indoor saltwater pool faces the Atlantic and is heated for year-round swimming.
Stay

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Winter tip Only some LIRR trains run through to Montauk without a change, and winter frequency is lower than in summer, so check the train you want in the MTA TrainTime app before committing to a Friday-night arrival.

3 hr 54 min
Photograph · Kyle Klein / Meet Boston
Massachusetts, USA

Boston

About 3 hr 55 min by Amtrak Acela, Moynihan Train Hall to Boston South Station (Amtrak timetable)Weekday Acela departures at 11:40 a.m., 2:01 p.m. and 6:05 p.m. reach South Station in 3 hr 53 min to 3 hr 59 min, stopping at Providence about 3 hr 5 min out.

Meet Boston's Frostival gives late winter a centre of gravity: a free lodge of furnished living rooms, glass-enclosed firepits and curling in Copley Square, with a Ferris wheel on the Greenway from early February. The Isabella Stewart Gardner Museum's courtyard moves from Midwinter Tropics to orchids over the same weeks.

Time it for Boston Frostival 22 Jan – 5 Mar 2027

Meet Boston's citywide winter festival, anchored by the free Frostival Lodge in Copley Square.

Do
  • Frostival Lodge, Copley Square Free lodge with six furnished living rooms, glass-enclosed firepits, a bar and curling, open daily 11 a.m. to 9 p.m., 22 January to 5 March 2027.
  • Isabella Stewart Gardner Museum courtyard Seasonal plantings rotate from A Holiday Garden (December to January) to Midwinter Tropics (January to February) and Orchids (February to March).
  • Frostival Ferris Wheel Meet Boston lists a 75-foot wheel on the Rose Kennedy Greenway arriving in early February 2027; dates and tickets not posted as of 20 Oct 2026.
Stay
  • Fairmont Copley Plaza Opened on 19 August 1912 on the former Copley Square site of the Museum of Fine Arts, a few steps from the Frostival Lodge.
  • The Newbury Boston Opened in 1927 on the corner of Arlington and Newbury Streets, its cocktail service historically "overlooking The Public Garden"; home to Contessa.

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Winter tip Meet Boston says Dine Out Boston returns for two weeks in winter 2027 but has not set dates; the 2026 edition ran 22 February to 7 March, which overlapped the lodge's final weeks.

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A short flight 2 trips

1 hr 30 min
Photograph · Victor Diaz Lamich / Montréal en Lumière
Montréal, Québec, Canada Passport needed

Montréal

About 1 hr 30 min nonstop from JFK, LaGuardia or Newark, per Tourisme MontréalMontréal-Trudeau is 20 km from downtown and the 747 express bus takes 45 to 70 minutes. Amtrak's daily Adirondack runs from Moynihan Train Hall to Montréal in about 12 hours.

Montréal runs two winter festivals back to back: Igloofest's outdoor electronic music nights in the Old Port, then Montréal en Lumière, which ends with a free all-night Nuit blanche. Bota Bota, a floating spa in the Old Port, is the warm counterweight.

Time it for Montréal en Lumière 18–28 Feb 2027

Late-winter festival with an outdoor site, skating trail, light works and food, ending with Nuit blanche on 27 February.

Do
  • Igloofest Outdoor electronic music festival at the Old Port, 14 January to 6 February 2027 per Tourisme Montréal.
  • Nuit blanche Free all-night program in the Quartier des spectacles near Place-des-Arts on Saturday 27 February 2027.
  • Bota Bota, spa-sur-l'eau Floating spa in the Old Port since 2010, adding a second boat designed by Sid Lee Architecture in winter 2026.
Stay
  • Hôtel William Gray Old Montréal hotel overlooking Place Jacques-Cartier, with the Perché rooftop and its own spa.
  • The Ritz-Carlton Montréal On Sherbrooke Street West since 1912, with Maison Boulud and Spa St. James's indoor saltwater pool.

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Winter tip Montréal en Lumière overlaps the NYC Midwinter Recess (15 to 19 February 2027) and Nuit blanche falls the following Saturday, so book flights and hotels for either week early; Americans need a passport for the flight.

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2 hr 5 min
Photograph · P. Hughes / Wikimedia Commons (CC BY-SA 4.0)
Bermuda Passport needed

Bermuda

Just over 2 hours nonstop on JetBlue from JFK, per the Bermuda Tourism AuthorityBermuda's airport offers US Customs and Border Protection preclearance before departure, so there are no further formalities on arrival home.

Bermuda is the warm-weather escape on this list, just over two hours from JFK with daytime winter temperatures around 70°F (21°C). Winter is its quiet season, built around Restaurant Weeks in January and February, Spa Month in February and golf on seven courses.

Time it for Bermuda Restaurant Weeks 2027 dates still to be announced; ran 16 January to 16 February in 2026

The island's biggest culinary promotion of the year.

Do
  • Bermuda Spa Month February promotion across the island's spas, including treatments in its caves.
  • Golf The tourism authority lists seven courses playable all year.
  • St. George's bus tour Three-hour guided excursion to the UNESCO World Heritage town of St. George's.
Stay
  • Rosewood Bermuda 88 rooms and suites on 240 coastal acres in Hamilton Parish over Castle Harbour, with the par-70 Tucker's Point course, SENSE spa and what it calls the largest private pink-sand beach on the island.

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Winter tip Entry needs a valid passport, a round-trip ticket and the digital Bermuda Arrival Card, which the tourism authority recommends completing before you fly.

The season

The winter calendar

The dates that make a winter trip, as the organisers have announced them. Events still waiting on 2027 dates are listed with their trip, not here.

November 2026

  • 21 Nov 2026 – 3 Jan 2027Holidays at the Newport MansionsNewport
  • 27 Nov 2026 – 28 Feb 2027RiverRink WinterfestPhiladelphia

December 2026

January 2027

February 2027

March 2027

NYC Public Schools close for Winter Recess from 24 December 2026 to 1 January 2027 and for Midwinter Recess from Monday 15 to Friday 19 February 2027. Acela seats, ski lessons and Montréal hotels go early for both. School holidays in New York City →

Questions

Quick answers

What are the best winter weekend getaways from NYC without a car?

Philadelphia is about 1 hour 10 minutes by Acela, Beacon about 80 minutes by Metro-North from Grand Central, Hudson about 2 hours by Amtrak, Providence about 3 hours and Washington about 3 hours and Boston just under 4 hours by Acela. Montauk is about 3 hours 10 minutes on the LIRR's direct weekend trains.

What is a romantic winter getaway near New York City?

Mohonk Mountain House, Wildflower Farms and Inness are all about 90 minutes north in the Shawangunk Ridge country. Further out, Castle Hill Inn in Newport sits on its own 40-acre peninsula, and Twin Farms in Vermont is all-inclusive and for adults 14 and over.

Where can you ski near New York City?

Hunter Mountain is about 2 hours 30 minutes away by car, with Belleayre nearby in the Catskills. Lake Placid's Whiteface is about 5 hours, Woodstock, Vermont about 4 to 4.5, and Stowe about 6.5, or a short flight to Burlington plus a 40-minute drive.

What is on during NYC's Midwinter Recess in February 2027?

Midwinter Recess runs 15 to 19 February 2027. Montréal en Lumière opens on 18 February, Boston's free Frostival Lodge is open daily until 5 March, and Bermuda's winter daytime temperatures average about 70°F.

When are the big winter festivals near New York in 2027?

Igloofest in Montréal runs 14 January to 6 February and Montréal en Lumière 18 to 28 February. Lake Placid hosts World Cup ski jumping and Nordic combined from 5 to 7 February, Boston's Frostival Lodge is open 22 January to 5 March, and the Philadelphia Flower Show runs 13 to 21 March.

What are the best winter getaways from New York by car?

The closest are Mohonk & the Shawangunks (1 hr 30 min), Hunter & the Catskills (2 hr 30 min), The Berkshires (2 hr 30 min), Cape May (3 hr). Times are the tourism boards' own figures from downtown in normal conditions; allow more in snow.

Where can you go from New York by train in winter?

By train: Philadelphia (1 hr 11 min), Beacon & Dia Beacon (1 hr 20 min), Hudson & Olana (2 hr), Washington, DC (2 hr 57 min). Rail skips winter driving entirely; book early for school-holiday weeks, when trains sell out.

Do I need a passport for these trips?

Only for the trips that cross a border: Montréal, Bermuda. Check passport and entry rules for your nationality before booking; everything else on this list is domestic.

Sources (105)

Checked 21 October 2026. Dates change: confirm with the event or hotel before you book. Spot something out of date? Tell us via our corrections policy.

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