1. SHARPE HILL VINEYARD
Connecticut’s aptly named Quiet Corner takes on a pastoral feel in winter, especially with snow blanketing the ground. Tucked into this Rockwell-esque scene is a hillside winery that’s tough to find but tougher to leave — its 1700s-era house and barn are straight out of a movie. In a tasting room with the feel of an elegant country home, sample from Sharpe Hill’s array of excellent wines (including the cabernet franc if you’re into bold, Bordeaux-style reds) and soak in the enchanting atmosphere of this spot just a 90-minute drive from Boston. – Marc Hurwitz
Details: 108 Wade Road, Pomfret, Connecticut, 860-974-3549, sharpehill.com
2. EAGLE WATCHING
On the day the Shepaug Bald Eagle Observatory in southwestern Connecticut opened for the winter last year, 15 of the majestic birds greeted visitors by soaring above the Shepaug Dam. Eagles that spend the winter in New England just can’t stay away — and you don’t have to stand outside in the cold to watch them. A small wooden observatory overlooks the 147-foot-high dam. The pool at the base never freezes and the turbulent churn brings fish to the surface. It’s an all-you-can-eat buffet for eagles in the know. Open December 23 to March 10, on Wednesdays, Saturdays, and Sundays, from 9 a.m. to 1 p.m. Free, but reservations required at bookeo.com/shepaug-eagle-viewing. – Patricia Harris and David Lyon
Details: 2225 River Road, Southbury, Connecticut, facebook.com/baldeagles
MAINE
3. “SECRET” VISTA AT SUNDAY RIVER
The overlook atop Sunday River’s Barker Mountain is something of an open secret: an unmarked, well-trodden rock ledge offering one of the most charming peak views in the state. To get there from the lift, start down the beginner-friendly Three Mile Trail. Pause just before the first bend where you’ll likely see a smattering of (temporarily) abandoned skis on your left. Ditch yours safely (but hang onto your poles) and hike 20 or so yards into the trees along a faint, snowy path, past evergreens decorated with empty nips of Fireball whiskey. At the flat rock peak, you’ll find two Adirondack chairs (vacant, if you’re lucky) and an expansive south-facing view: mountains, trees, sky. But if anyone asks, you didn’t hear about it from me. – Alyssa Giacobbe
Details: 15 South Ridge Road, Newry, Maine, 207-824-7669, sundayriver.com
4. CANDLELIGHT CAROLING
Kennebunkport’s Christmas Prelude, an 11-day annual celebration to usher in the season, may be known for its decidedly merry vibe, but the breakout stars are a group of Franciscan monks singing traditional carols. For one night, the grounds of St. Anthony’s Monastery light up for a magical outdoor performance by candlelight. Flames flicker through the crowd as the candles are lit, telephone-style — accept a flame, and maybe a holiday greeting, from your neighbor and pass it on. You needn’t be religious or even celebrate Christmas to experience a little bit of what this time of year is, as they say, really about. This year’s caroling event, which is free, takes place December 2 at 6:30 p.m. – Alyssa Giacobbe
Details: 28 Beach Avenue, Kennebunk, Maine, 207-967-2011, christmasprelude.com
5. GARDENS AGLOW
Imagine 750,000 twinkling LED lights in every direction as you stroll through the magical world that is Gardens Aglow at Coastal Maine Botanical Gardens. Bundled up, and with a thermos of cocoa, you walk through 14 acres of gardens, bathed in the light of illuminated sculptures, trees, and structures. Time seems to pause for the hour or so it takes to make your way through. Once you go, you’ll want to make this an annual tradition like my family has. Through December 31. – Erinne Magee
Details: 105 Botanical Gardens Drive, Boothbay, Maine, 207-633-8000, mainegardens.org
6. CENTRAL PROVISIONS
Every winter, my friends and I gather at a low-slung, brick-walled Portland restaurant that’s a passageway to another world: a cross between Cheers and Beowulf. Here, the clouds are lined with charcuterie. Pungent, runny cheese flows as the wind and snow howl outside. Gluttony is expected; the faint aroma of whiskey fills the air. Within this cozy refuge, linger over spoonfuls of bone marrow and toast; slather on the red-onion jam a little thicker. Laughter ricochets off the brick walls as darkness falls. What’s one more glass of wine? – Kara Baskin
Details: 414 Fore Street, Portland, Maine, 207-805-1085, central-provisions.com
7. JACK WILLIAMS TOBOGGAN CHUTE
Built in 1936, this toboggan chute in Camden, Maine, is one of the last of its kind in the country: a 400-foot-long wooden trough packed with ice. Clamber to the top, climb in, and hold on! You’ll fly at speeds up to 30 miles per hour, rumbling and roaring through the woods before sliding across frozen Hosmer Pond. Named after a key figure in the chute’s revitalization, the slide harkens back to a time of simpler thrills. It’s also home to the US National Toboggan Championships, held the first weekend in February, when you can cheer on contestants or register to join. The chute is $10 per person, per hour; free toboggans available to use. Must be 42 inches tall to ride. See website for schedule and other details. –Diane Bair and Pamela Wright
Details: 20 Barnestown Road, Camden, Maine, 207-236-3438, camdensnowbowl.com/toboggan-chute
MASSACHUSETTS
8. SUNRISE OVER CHATHAM
The vivid hues of a Cape Cod sunrise are even more spectacular during the cold months, and (bonus!) you don’t have to get up as early to see them. For front-row seating, park at the Chatham Lighthouse Beach lot and watch from the cozy warmth of your car, sheltered from the icy winds whipping off the water. Pull up your playlist or simply enjoy the sounds of the waves and the gulls overhead. Unlike summer, there’s no limit to how long you can stay, but a cup of freshly brewed coffee at Chatham Perk beckons. – Julie Suratt
Details: 42 Main Street, Chatham, 508-945-5199, chathaminfo.com/beaches
9. COCOA ON COMM AVE
Winter in Boston can feel grim, especially after the first snow goes gray with dirt and slush. One way to make the most of the dark days: Arm yourself with a hot chocolate from the L.A. Burdick Handmade Chocolates near Copley Square and wander the Commonwealth Avenue Mall under trees wrapped in string lights, past the occasional brownstone festooned in holiday finery. With a friend or a date, you’ve got the perfect dose of dreamy Hallmark-movie magic. It’s a quick stroll, just long enough to leisurely sip your drink — and with the perfect bit of sparkle to take the edge off those 4:30 p.m. sunsets. – Elizabeth Koh
Details: 220 Clarendon Street, Boston
10. SANTA BY THE SEA
It’s the first Saturday in December, and we’re huddled by the harbor in Rockport, braving the briny chill to watch Santa Claus pull into town — by lobster boat. After docking, Santa hops aboard an antique firetruck and poses for pictures at a nearby church, but we spend our afternoon strolling art galleries, gift shops, and cafes along Bearskin Neck, scooping up holiday presents and cozy treats. Later, a choir sings carols in Dock Square beneath a towering local spruce, whose 2,000 lights erupt as evening falls. The day is so quaint and wholesome, it feels like visiting Whoville — minus the Grinch. December 2, 1 p.m.– 4:30 p.m. – Jon Gorey
Details: Rockport, rockportusa.com/christmas-in-rockport
11. ETERNAL GREEN AT THE GARDNER
When the trees look frail and bare, the Isabella Stewart Gardner Museum’s courtyard is a lush reminder of warmer times. The garden is in perpetual bloom, with year-round mild temperatures allowing for seasonal displays that rotate nine times a year. Come winter, junipers, amaryllis, pines, palms, and ferns add bursts of color to the breathtaking Venetian Gothic architecture. Sit on the stone steps, crack open a book, and lose track of time. The stillness of the courtyard and the vibrancy of the impeccably tended plants are sure to revive your spirits. Tickets required — $20 adults, $18 seniors, $13 students, free for children under 18. – Zenobia Pellissier Lloyd
Details: 25 Evans Way, Boston, 617-566-1401, gardnermuseum.org
12. SUFGANIYOT AT KUPEL’S
Napkins at the ready, I sink my teeth into a raspberry-filled jelly doughnut coated in powdered sugar. Light and pillowy, but heavy once you hit the fruit filling, the sufganiyot from Kupel’s Bakery in Brookline are one of my Hanukkah traditions. Like other Hanukkah treats, they are fried in oil to pay homage to the miracle of the lamp oil that lit the menorah for eight days. Kupel’s version, sold from a week before Hanukkah (which this year begins at sunset on December 7) until a week after it ends (or when the store runs out), typically comes with raspberry or chocolate filling. Afterward, I stroll through the neighborhood that, with its kosher grocery and Judaica stores, is like a miniature of Jerusalem’s Jewish Quarter. Because it’s never just the scrumptious sufganiyot that I crave. – Linda K. Wertheimer
Details: 421 Harvard Street, Brookline, 617-566-9528, kupelsbakery.com
13. FESTIVAL OF LIGHTS
Every year until I was 6 or 7, my parents bundled me up for a pilgrimage to the National Shrine of Our Lady of La Salette in Attleboro for its annual Christmas Festival of Lights. Established in 1953 as part of the Catholic shrine’s ministry, the 10-acre site is bedecked with over 300,000 lights in a dazzling array of colors, illuminating its serene wooded landscapes, icons, grottos, and, the centerpiece, a pond surrounded by the Stations of the Cross with a crucifix sculpture at its center. It shines brightly as a tradition that has illumined New Englanders year after year. Through January 1, from 5 p.m. to 9 p.m. daily. Free. – Kevin G. Andrade
Details: 947 Park Street, Attleboro, lasaletteattleboroshrine.org/christmas-festival
14. VOLUNTEERING AT HALEY HOUSE
Few things brighten the winter more than giving back — and few places give more than the storied soup kitchen at Haley House. It’s not just the 50 to 100 meals its staff hands out to the community almost every day, rain or shine. There’s something about volunteering in the kitchen—brewing carafes of coffee, washing armfuls of produce, packing breakfasts in an assembly line — that turns cooking into community, strangers into friends. It’s a kind of magic Haley House has kept going for more than 50 years—and one that will keep you coming back, all year round. – Elizabeth Koh
Details: 23 Dartmouth Street, Boston, 617-236-8132, haleyhouse.org/volunteer
15. LYMAN PLANT HOUSE AND CONSERVATORY
When the holidays are over and everything is still frozen, I head to Lyman Plant House and Conservatory at Smith College in Northampton for a blast of warmth and late season cheer. Here, my dreams of summer are free to roam through rooms of camellia, citrus, and orchids; my kids love the waterfall and the banana tree (with actual bananas!), and the shiny pods of cacao they can’t believe make real chocolate. In the depths of February, there’s no better antidote to endless winter than the sun warming your bones through the glass walls, promising a return to sweeter days. – Francie Lin
Details: 16 College Lane, Northampton, 413-585-2742, garden.smith.edu
16. DINNER AT PAMMY’S
Rare is the restaurant that holds its charm after being discovered by the masses. Pammy’s in Central Square is a shining exception, and on cold winter evenings, it’s the perfect respite. One needs neither a reservation nor pomp to sneak into a fireside high top in the restaurant’s bar and lounge area. The wait is seldom longer than 30 minutes — just enough time for a pint at the nearby Plough and Stars. If I’m feeling spicy, I opt for the generous “choose-your-own-adventure” fixed menu ($79) and a Sazerac that rivals those mixed in New Orleans. When I need a familiar hug, it’s the gochujang Bolognese and Miller High Life. For parties larger than three or four, a reservation is strongly suggested. – Hanna Krueger
Details: 28 Massachusetts Avenue, Cambridge, 617-945-1761, pammyscambridge.com
17. GIBBET HILL GRILL
Drive west on Route 119 into Groton (est. 1655), turn right when you see the Old Groton Meeting House (1755, cover of Life magazine, November ‘42), and stop by the picturesque Gibbet Hill Grill. Inside the comfy bar area, you’ll discover an 8-foot-long gingerbread house resting on the fireplace mantel — lovingly detailed each year by three generations of Grill proprietors. Through the years, the candy-covered house has been decorated to simulate downtown Groton, the Boston skyline, Buckingham Palace, and Charles Dickens’ A Christmas Carol. The experience is warm, cozy, and takes you back in time. Enjoy a seasonal special Christmas cosmo or snowball martini by the 33-foot-tall, handmade granite fireplace. Gingerbread house displayed from day after Thanksgiving until New Year’s Eve. – Dan Shaughnessy
Details: 61 Lowell Road, Groton, 978-448-2900, gibbethillgrill.com
18. ENCHANTED VILLAGE
If you’re nostalgic for holidays past, head to the Enchanted Village at Jordan’s Furniture in Avon. Originating at the Jordan Marsh Downtown Crossing store in the ‘60s, the grand holiday display eventually fell into disrepair and bounced from one home to another. In 2009, Jordan’s Furniture bought its surviving pieces – the animatronic carolers, shoppers, and revelers who occupy a variety of twinkling scenes – and restored them to all their Dickensian glory. Now the experience includes rides, skating, and games; you can even try the famous Jordan Marsh blueberry muffins, reproduced with loving authenticity. It’s a New England tradition. Through January 1. Some attractions require tickets. – Stephanie Tyburski
Details: 100 Stockwell Drive, Avon, 508-580-4900, jordans.com/enchanted-village
NEW HAMPSHIRE
19. GLEN HOUSE BAR
One joy of hitting the slopes or trails in winter is cozying up with a beverage afterward. In the shadows of Mount Washington sits a rustic lounge in a hotel with roots back to the 1800s, whose atmosphere is a nod to the grand hotels of New Hampshire’s past. Relax by the roaring fireplace with a beer, wine, or cocktail, then pop outside for a stunning view of the highest peak in the Northeast. Close to Wildcat Mountain and Pinkham Notch, it’s the perfect place to warm up and fuel the soul for another day of fun. – Marc Hurwitz
Details: 979 N.H. Route 16, Gorham, New Hampshire, 603-466-3420, theglenhouse.com
20. MT. MONADNOCK
Mount Monadnock, in Jaffrey, is less than two hours from Boston, which is among the reasons it’s one of the most climbed mountains in the world. On autumn weekends, its main trails can feel as jammed as the Southeast Expressway. But in the winter, when snow is high, the air bracingly cold, it can feel like yours alone. It is a magical — and challenging — winter hike, often requiring the use of traction devices such as crampons. On perfect, bright, and still winter days, when the trees are coated in delicate rime, the well-trod mountain becomes someplace new. – Mark Arsenault
Details: Monadnock State Park, 169 Poole Road, Jaffrey, New Hampshire, 603-532-8862, nhstateparks.org
21. ICE CASTLES
Some 25,000 tons of ice. About 12,000 icicles. Ice-carved caverns and caves, chutes and slides. The Ice Castles in North Woodstock, New Hampshire, sprawled across about an acre, are by no means tiny — and the display has become an essential experience of New England winter. Made entirely by hand, it’s a massive ice-scape that takes four weeks to construct, and delights and awes visitors throughout the season (typically early January through mid-March, weather permitting). There’s also tubing, horse-drawn sleigh rides, and an illuminated forest walk. See website for schedule and prices. –Diane Bair and Pamela Wright
Details: 24 Clark Farm Road, North Woodstock, New Hampshire, icecastles.com
22. A SEA SHANTY SINGALONG
Tucked in the backwoods of New Hampshire lies Canterbury Aleworks, a one-man pub with a roaring fire. You’ll know you’re there when you see a British phone booth outside. And every second Thursday of the month, “Shanty Man” Mike Green leads the crowd in a call-and-response sea shanty singalong. For two rollicking hours, amid the smiles and nanobrews (yes, micro is too big a measurement for this brewery) and eclectic crowd, it doesn’t matter how cold or dark it is outside. What matters is that when Mike bellows, “Oh, whiskey is the life of man,” you respond, “whiskey, whiskey, whiskey-o.” Tickets required — see website for details. – Hanna Krueger
Details: Canterbury Aleworks, 305 Baptist Hill Road, Canterbury, New Hampshire, 603-491-4539, canterburyaleworks.com
23. PUDDLE DOCK POND SKATING
Ice skating at Puddle Dock Pond is like gliding through a folksy Grandma Moses painting. Nestled next to the houses of Strawbery Banke Museum, an outdoor history museum in Portsmouth, an afternoon at the Zamboni-glazed pond is a trip back in time. The houses themselves, which show a neighborhood’s evolution over 350 years, are closed until spring — but bundle up and hit the ice for plenty of winter reveling. Check the schedule if you want to join a pick-up hockey game. Season lasts at least through February. See website for schedule and prices. –Patricia Harris and David Lyon
Details: 14 Hancock Street, Portsmouth, New Hampshire, 603-422-0600, strawberybanke.org
RHODE ISLAND
24. PROVIDENCE ATHENÆUM
When winter’s winds cut to the bone, the Providence Athenaeum beckons me to shelter among its nearly 180,000 books. With roots going back to 1753, the subscription library is among the oldest in the United States. Though a paid annual membership is needed to check out materials, a stroll through its three stunning floors — once frequented by the likes of H.P. Lovecraft and Edgar Allan Poe — is free. Grab a hot chocolate from a nearby coffee shop, find a book, and settle in for a good afternoon read. – Kevin G. Andrade
Details: 251 Benefit Street, Providence, 401-421-6970, providenceathenaeum.org
25. WATCH HILL OYSTERS
Oysters are at their most succulent early in winter. And there are few places more picturesque to gather them than along Westerly’s Watch Hill peninsula, where Taylor Swift’s seaside villa is perched. A caveat: Harvesting oysters and clams isn’t allowed in areas where commercial shellfishers have staked a claim. But East Beach, Maschaug Pond, and other east-facing spots are fair game, and all you need is a rake, some boots, and a permit ($11 for nonresidents). Hunt your winter quarry to the siren song of everyone’s favorite local mansion mermaid: “And it’s like snow at the beach / Weird, but [expletive] beautiful.” – William J. Kole
Details: 227 Shore Road, Westerly, Rhode Island, 401-322-7280, dem.ri.gov
26. NEWPORT MANSIONS
Newport usually screams summertime, but the winter has its own charm on this part of the Rhode Island coastline. After all, what better time than winter to spend an afternoon inside — and the Newport mansions make it easy to while away hours wandering. The Breakers is the largest and most ornate — more so during the holiday season. It’s one of three mansions that put up decorations annually, from dozens of baubled trees and evergreen garlands to the 15-foot-tall poinsettia tree. See website for schedule and prices. – Elizabeth Koh
Details: 44 Ochre Point Avenue, Newport, newportmansions.org
VERMONT
27. GET COZY AT PITCHER INN
Never have the words “meet me by the fireplace” sounded cozier — or tastier — than at The Pitcher Inn in Warren. Executive chef Jacob Ennis employs the inn’s massive brick hearth for his “fire-to-fork” menu offered in winter, roasting meats and simmering cauldrons of soup over an open wood fire. Humble root vegetables such as celeriac, sweet potatoes, and rutabaga emerge as superstar side dishes. Corn bread and other old-fashioned pan breads, complemented by homemade burrata and ricotta cheese, round out the perfect winter dining experience. Don’t wait too long: The winter menu only lasts through the end of the ski season. – Diane Bair and Pamela Wright
Details: 275 Main Street, Warren, Vermont, 802-496-6350, pitcherinn.com
28. HORSE-DRAWN SLEIGH RIDES
Snow isn’t just for skiers; you might prefer snuggling under blankets for an old-fashioned sleigh ride. Kedron Valley Stables in South Woodstock offers stunning trips, lasting 45 minutes to an hour, through open fields and around their wooded edges, provided the ground is frozen and there’s enough snow. Owner Chip Kendall, whose family has been in the valley since the late 1700s, loves the landscape like he loves the horses. And, yes, the sleigh bells do jingle. Rides, which leave from the Green Mountain Horse Association, cost $200 for one to three people; $300 for four to five. Reservations required. – Patricia Harris and David Lyon
Details: 5491 South Road, South Woodstock, Vermont, 802-457-1480, kedron.com
29. VON TRAPP BIERHALL
Every winter, a beautiful pocket of Vermont comes alive with cross-country skiers and snowshoers enjoying the fields, meadows, woods, and mountain scenery at the Trapp Family Lodge’s historic cross-country ski center. After a day on the trails, head over to this rustic Austrian-style bierhall for easy-drinking pilsners, floral helles lagers, crisp Kölsch-style ales, and other beers with European (and New England) influences. Its wooden beams, communal tables, hanging lights, and mesmerizing valley views almost make it feel more like a ski lodge than a brewpub, which makes it the perfect place to end a tranquil day of Nordic sports. – Marc Hurwitz
Details: 1333 Luce Hill Road, Stowe, Vermont, 802-253-5750, vontrappbrewing.com
30. THE SINGLE CHAIRLIFT AT MAD RIVER GLEN
Some of my favorite ski days are the solo ones, when I wake up to the sunrise and decide, in that dawn moment, to rip it up to Vermont, accompanied by an audiobook, a thermos of coffee, and a PB&J. On days like these, my destination is often the venerable, co-op-owned Mad River Glen. Suit up in the parking lot (pro tip: put your rubber car mat on the ground so your socks don’t get wet) and head straight to the mountain’s single chairlift, the only lift of its kind in the Lower 48. It’s a testament to old-school New England skiing on a small, but mighty, mountain — and a rare moment of solitude. – Hanna Krueger
Details: 57 Schuss Pass, Waitsfield, Vermont, 802-496-3551, madriverglen.com
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