Out & About | Best New England Winter Events for 2019

From thrilling ski contests to tasty food festivals, we’ve rounded up regional events that are worth the drive.

By Yankee Magazine

Dec 20 2018


Built in 1922 and reopened in 2009 after a major renovation, Vermont’s Harris Hill is a showcase for Olympic-hopeful ski jumpers during its Fred Harris Memorial Tournament.

Photo Credit : Heather Marcus


Built in 1922 and reopened in 2009 after a major renovation, Vermont’s Harris Hill is a showcase for Olympic-hopeful ski jumpers during its Fred Harris Memorial Tournament.
Photo Credit : Heather Marcus


The Sun Wine & Food Fest JAN. 24–27

It may be winter, but there’s plenty of fun in the Sun—the Mohegan Sun resort casino, that is—during this sprawling showcase of beer, wine, specialty spirits, and delectable dishes. Among the highlights are a grand tasting with 1,000-plus varieties of wine, beer, and spirits being poured and celebrity chef appearances by the likes of Bobby Flay and Marcus Samuelsson. Uncasville, CT.


Pies on Parade JAN. 27

Come explore the meaning of pie as the town of Rockland hosts a day devoted to this classic baked treat. Stroll among area restaurants and historic inns for samples of 50-plus kinds of pies, from sweet to savory—but be sure to buy your ticket early, as this event sells out fast. Rockland, ME. 207-596-6611;


Railroad Hobby Show JAN. 26–27

For an opportunity to behold more than nine acres of railroad-centric displays and attractions—including more than 60 model train layouts, a flea market, art shows, and Peppersass, Mount Washington’s first cog railway locomotive—make tracks for the Eastern States Expo, home to the largest train show in North America. West Springfield, MA. 413-267-4555;


Hood Museum of Art Grand Reopening JAN. 26

In a fitting kickoff to Dartmouth College’s 250th anniversary year, the school’s world-class art museum finally reopens after a three-year, $50 million makeover. Come look for your favorite artworks and discover new ones on an opening day enlivened with refreshments, giveaways, and live music.Hanover, NH.


Providence Children’s Film Festival FEB. 15–28

Though the schedule was still under wraps at press time, we’re betting the 10th anniversary edition of this festival will be a hot ticket. Count on a rich slate of independent features and short films from around the world, plus postfilm discussions, workshops for kids, and a young filmmakers showcase. Providence, RI. 401-209-7585;


Fred Harris Memorial Tournament FEB. 16–17

Ski jumping, the original extreme sport, returns to Harris Hill for a winter spectacle that truly must be seen to be believed. At the only 90-meter ski jump in New England, you can watch jumpers up close as they launch themselves from the top and soar more than 300 feet at speeds up to 60 mph. Brattleboro, VT.



JAN. 5–6: HARTFORD, Connecticut Wedding & Bridal Expo. The largest event of its kind on the East Coast sets up shop at the Connecticut Convention Center, combining fashion shows with dozens of vendors to offer one-stop shopping for any and all wedding needs. 860-365-5678;

JAN. 18–20: EAST HADDAM, Festival of New Musicals. Emerging artists premiere recently completed musical works, each of which was brought to life with the guidance and resources of the famed Goodspeed Opera House. 860-873-8668;

FEB. 8–10: SALISBURY, Jumpfest. For nearly a century, the Salisbury Winter Sports Association has been holding this annual ski jumping competition on Satre Hill, drawing competitors from far and wide and crowds to cheer them on. 860-850-0080;

FEB. 9: PUTNAM, Fire & Ice Valentine’s Festival. At the largest single-block ice carving competition in the U.S., artists transform 300-pound chunks of frozen water into sparkling masterpieces. Factor in live carving demonstrations, fire dancers, carriage rides, and chocolate sculptures, and you have a community celebration that’s too cool to pass up.

FEB. 9–10: WILLIMANTIC, Romantic Willimantic Weekend. More than 30 downtown businesses will be serving up an assortment of chocolate-inspired treats during a weekend of fun that will also see a cake baking contest and a pub crawl. 860-428-7573;

FEB. 10: RIDGEFIELD, iLuminate. This one-of-a-kind dance troupe that first rose to fame on America’s Got Talent uses special light suits that enable its members to disappear, reappear, and seemingly fly as they perform to music by Michael Jackson, Bruno Mars, Sam Smith, and more. 203-438-5795;

FEB. 13–MAR. 10: NEW HAVEN, “Tiny Beautiful Things.” Based on the book by best-selling author Cheryl Strayed (Wild) and adapted for the stage by Nia Vardalos (My Big Fat Greek Wedding), this play is about an anonymous online advice columnist who, in helping her readers, finds a way to heal herself as well. 203-787-4282;

FEB. 21–24: HARTFORD, Flower & Garden Show. Spring arrives early at the Connecticut Convention Center, where more than 300 booths are overflowing with fresh flowers, plants, herbs, bulbs, and seeds, not to mention gardening books and informational sessions galore. 860-844-8461;

FEB. 22–JUNE 2: NEW BRITAIN, “The Beyond: Georgia O’Keeffe and Contemporary Art.” Nearly three dozen works by the mother of American modernism anchor this exploration of modern art, which also features work by 20 emerging contemporary artists. 860-229-0257;

FEB. 23: MYSTIC, Cabin Fever Festival & Charity Chowder Cook-off. Stroll the groundsand get in a bit of shopping at Olde MistickVillage before sampling the various tastychowders prepared by chefs from across theregion. 860-536-4941;


JAN. 1: OLD ORCHARD BEACH, Lobster Dip. Maine’s original and largest ocean dip celebrates its 32nd year, as more than 300 hardy souls take to the chilly water in front of the Brunswick resort (weather permitting) to support Special Olympics Maine. 207-879-0489;

JAN. 7–11: NEWRY, Children’s Festival. Sunday River offers an entire week dedicated to families that allows kids to ski and stay for free. The fun will include fireworks, scavenger hunts, tubing, evening performances, and dinners with Eddy the Yeti. 207-824-3000;

JAN. 11–13: AUGUSTA, Northeast Motorsports Expo. This show at the Augusta Civic Center provides racing fans a great opportunity to meet drivers, get autographs, check out race cars, and talk shop with the experts.

JAN. 13: BATH, Bath Antique Show. Bath Middle School hosts 50-plus antiques dealers from all over New England at this venerable show, still going strong more than three decades on. From toys and furniture to paintings and collectibles, you never know what you’ll find. 207-832-7798;

JAN. 19–20: BANGOR, SnowCon. Back-to-basics entertainment is the name of game at the Cross Insurance Center, where the focus is on board, card, and tabletop games, with ample opportunity to browse, play, and buy.

FEB. 1–28: BRUNSWICK, Longfellow Days. To honor the life and works of this famed poet and former Bowdoin College student, the Brunswick community hosts a month of readings, lectures, tours, dining events, and film screenings at venues around town. 207-729-4439;

FEB. 8–10: CAMDEN, U.S. National Toboggan Championships. Some 400 sledders take to the historic Jack Williams Toboggan Chute at the Camden Snow Bowl to compete for the fastest time—and to sport zany and creative costumes.

FEB. 16–17: PORTLAND, Maine Home & Remodeling Show. With more than 180 exhibitors and a long lineup of expert-led seminars, Cross Insurance Arena has everything you need to shake off the winter blahs and start planning for an inspired spring of home and garden projects. 207-321-4246;

FEB. 17: SOUTH BRISTOL, Ice Harvest. Visit the Thompson Ice House to see how ice was harvested in the 19th and early 20th centuries. After watching the cutting and lending a hand with the transportation of the ice blocks, you’ll still have plenty of time for skating, horse-drawn wagon rides, and a visit to the museum.


JAN. 4–6: NEW BEDFORD, Moby-Dick Marathon. Join in the New Bedford Whaling Museum’s annual read-a-thon of one of America’s most enduring novels. 508-997-0046;

JAN. 10–13: WILLIAMSTOWN, I/O Festival of New Music. Focusing on unconventional spaces and modes of performance, this annual highlight of the Williams College calendar offers talks, workshops, and music by visiting artists as well as students and faculty. 413-597-2425;

JAN. 11, 25: Sturbridge, An Evening of Illumination. Experience life before electricity as you tour historic Old Sturbridge Village lit only by candles, oil lamps, lanterns, and firelight. The tour includes music and storytelling along the way, and concludes at the Bullard Tavern for light refreshments and a cash bar. 800-733-1830;

JAN. 17–20: CAMBRIDGE, Boston’s Celtic Music Festival. Soak up the sounds of more than 100 Celtic-inspired musicians, singers, and dancers at this event, now in its 16th year, at the storied Club Passim. 617-492-7679;

JAN. 17–21: BOSTON, New England International Auto Show. Behold the premier showcase of newest-model vehicles, both imported and domestic, at the Boston Convention & Exhibition Center. Test drives will be offered, and factory and dealer reps will be on hand to answer questions. 781-237-5333;

JAN. 26–27: HYANNIS, Cape & Islands Orchid Show & Sale. Bringing some much-needed color to midwinter, this event at the Resort and Conference Center at Hyannis provides expert advice on orchid care and maintenance, beautiful photo opportunities, and flowers to bring home.

FEB. 8–9: IPSWICH, Fire & Ice at Castle Hill on the Crane Estate. Magnificent ice sculptures, a roaring bonfire, and lots of dancing and eating combine for a chill-chasing new event at this historic seaside estate, one of the marquee properties owned by the Trustees of Reservations. 978-356-4351;

FEB. 8–10: SALEM, So Sweet Chocolate and Ice Sculpture Festival. This decadent tradition brings ice sculptures, wine tastings, deals on Valentine’s Day gifts, and plenty of chocolate, chocolate, chocolate to downtown Salem. 978-744-0004;

FEB. 9: NEWBURYPORT, Merrimack River Eagle Festival. Visit Joppa Flats Education Center for fun indoor and outdoor activities, and learn more about these magnificent birds and the habitat they share with us. 978-462-9998;

FEB. 22–24: BOSTON,New England Home Show. From lighting to flooring to siding, look for a wide range of home improvement ideas, tools, and techniques at the Seaport World Trade Center. Plus: cooking demonstrations, crafts, a furniture building zone, and specialty foods. 508-823-0389;

New Hampshire

JAN. 18–FEB. 17: NEW CASTLE, Winter Wine Festival. Pairing fine wines with great food and the hospitality of a grand hotel, this monthlong festival at Wentworth by the Sea offers everything from jazz brunches to oyster parties. 603-422-7322;

JAN. 25–27: JACKSON, New Hampshire Sanctioned and Jackson Invitational Snow Sculpting Competition. The most talented snow sculptors from across the region converge for a weekend of creating. Spectators are welcome throughout the process, but most pieces are not finished until Sunday. Nighttime illumination makes an after-dark stroll a must.

FEB. 1–2: MANCHESTER, New Hampshire Farm and Forest Expo. Billing itself as the state’s “greatest winter fair,” the Farm and Forest Expo promises a top-notch lineup of exhibits, demonstrations, and lots of fuzzy and furry animals at the Manchester Downtown Hotel.

FEB. 2: PORTSMOUTH, “Make America Grin Again.”The Capitol Steps, a troupe of former congressional staffers turned musical comedians, returns to the Music Hall for an annual concert to support affordable-housing development. 603-436-2400;

FEB. 3: HENNIKER, Vertical Challenge. This free, fun race at Pats Peak has skiers and snowboarders competing in more than 30 race categories. In between races, you’ll have plenty of time to enjoy the array of music and games. 603-428-3245;

FEB. 7-10: HANOVER, Dartmouth Winter Carnival. Look for polar bear swims, snow-sculpture contests, races, and more across the Dartmouth campus, all offered with a playful dose of Ivy League goofiness. 603-646-3399; dartmouth.edu

FEB. 7–10: NEWPORT, Newport Winter Carnival. Still going strong after more than 100 years, this townwide tradition includes pancake breakfasts, a snowball tournament, parades and pageants, and fireworks.

FEB. 8–10: NASHUA, New Hampshire Orchid Society Show & Sale. The Courtyard Marriott Nashua is the place to be if you’d like to meet some of the Granite State’s most accomplished orchid growers, get expert answers to your questions, and take in a whole lot of beauty.

FEB. 9–10: MEREDITH, Ice Fishing Derby. Ice fishing means bragging rights and cash prizes for those who reel in the big catch, and a day of fun and camaraderie for all. So purchase your derby pass, and hit the lakes. 603-279-7600;

FEB. 24: MOUNT WASHINGTON VALLEY, Chocolate Festival. Whether you choose to travel by car, ski, or snowshoe, this inn-to-inn tour through the Mount Washington Valley will keep you fueled with decadent goodies to sample along the way. 603-356-9920;

Rhode Island

JAN. 1: NEWPORT, Polar Bear Plunge. Take a cold dip for charity (or come out to lend moral support) as the Newport Polar Bears dive into the frigid Atlantic off Easton’s Beach. Proceeds from the swim and the after-swim party benefit A Wish Come True. 401-849-8048;

JAN. 3: EXETER, Winter Big Day. Register in advance for this popular bird-watching program, which begins at the Audubon Society’s Fisherville Brook Wildlife Refuge and lets you discover several winter birding hot spots through the course of the daylong van trip. 401-949-5454;

JAN. 13–26: PROVIDENCE,Restaurant Week. Your dieting resolutions can wait until February. During this twice-yearly culinary to-do, restaurants across the city offer wallet-friendly prix fixe lunches and dinners (and even some two-for-one specials).

JAN. 19–20: PAWTUCKET, Knitting Weekend & Fiber Market. Refine your crafting skills and stock up on supplies as Slater Mill celebrates fiber arts with a marketplace, workshops, and more. 401-725-8638;

FEB. 2: WESTERLY,Nordic Voices. As part of its Kent Hall Masters Series, the Chorus of Westerly welcomes this six-member a cappella group that’s been earning acclaim not only back home in Norway but also in South Africa, Taiwan, Bolivia, and the U.S. 401-596-8663;

FEB. 8–10: PROVIDENCE, Northeast International Auto Show. Check out all the latest models and newest features as one of the Rhode Island Convention Center’s most popular exhibitions returns. 401-458-6000;

FEB. 9: LINCOLN, Lincoln’s Birthday Celebration. Dig into a slice of cake at the Arnold House museum in honor of Honest Abe’s birthday as you learn about the 16th president’s visits to Rhode Island and how it was that the town of Lincoln came to be named for him. 401-728-9696;

FEB. 15–24: NEWPORT, Winter Festival. This annual extravaganza includes activities throughout the city (more than 160 events total) that collectively offer fine food, music, and entertainment for the whole family. 401-847-7666;

FEB. 23: WOONSOCKET,Mardi Gras Celebration. Honoring the area’s proud French-Canadian heritage, the festivities at St. Ann Arts and Cultural Center include live music, a delicious Cajun-inspired dinner, and cash bar, plus lots of costumes, of course.


JAN. 19: QUECHEE, Winter Wildlife Celebration. Visit the Vermont Institute of NaturalScience (VINS), the home of many wingedambassadors—from owls to eagles—for thisday that’s all about family-fun activities. Join expert educators to explore exhibits and trails, and enjoy games, crafts, and activities. 802-359-5000;

JAN. 13: STOWE, Stowe Derby. One of the most unusual ski races in North America provides participants with the ultimate test of their abilities. The race begins atop Mount Mansfield and concludes in the historic village of Stowe—and just one set of skis is allowed per competitor.

JAN. 24–FEB. 3: STOWE, Winter Carnival. From snow volleyball, snow golf, and broomball to ice carving, ski movies, karaoke, and a beer garden, there’s something for everyone at Stowe’s annual celebration of winter.

JAN. 29–31: ESSEX JUNCTION, Vermont Farm Show. The Champlain Valley Expo Center plays host to this annual tradition, which features more than 250 booths showcasing everything from beekeeping to sugar making to dairy farming. 802-461-8774;

FEB. 2: BARRE,Arrival from Sweden. Billed as the “most authentic ABBA show there is,” Arrival from Sweden has been bringing the hits of the immortal pop band to life for more than 20 years. Now the group hits the stage at the Barre Opera House to perform all of ABBA’s hits—and in appropriately over-the-top costumes. 802-476-8188;

FEB. 2–3: CRAFTSBURY COMMON, Craftsbury Marathon Doubleheader. The largest Nordic ski event in the East now comes with a twist: You can register for the classic marathon on Saturday, skiing either 25 or 50 kilometers on some of the most scenic terrain in New England, or opt for the new, slightly shorter freestyle marathon on Sunday. Or both! 802-586-7767;

FEB. 9: BURLINGTON, Brrrlington Winter Bash. The Miller Recreation Center hosts a free day of family fun both indoors and out, from dogsled races and snow fort building to crafts and dancing and food. 802-540-1058;

FEB. 15–17: WOODSTOCK, Vermont Flurry.Over Presidents’ Day weekend, professional snow sculpting teams descend on the village green to create stunning large-scale sculptures. 802-457-3981;

FEB. 16: NORWICH, Igloo Build. One of the Montshire Museum’s longest-running and most entertaining traditions returns, as igloo expert Bert Yankielun gives hands-on instruction on how to build an insulated, sturdy snow house. Fun for all ages, with indoor warm-up activities throughout the day. 802-649-2200;

FEB. 16–24: BRATTLEBORO, Brattleboro Winter Carnival. At this townwide party, you can see a movie, a puppet show, a concert, or a variety show; hit the ice rink or the dance floor; and still find time for cook-offs and pancake breakfasts, sleigh and snowmobile rides, and games.