Out & About | Best New England Winter Events for 2020

From pond hockey tourneys to polar bear plunges, these top New England winter events are worth the drive.

By Yankee Magazine

Dec 27 2019


Players from Boston’s Puckaneers and Belmont, New Hampshire’s Mainstay Solutions chase the puck behind the nets at the 2013 New England Pond Hockey Classic on Lake Winnipesaukee.

Photo Credit : Kathie Fife Photography

Best New England Winter Events for 2020

Players from Boston’s Puckaneers and Belmont, New Hampshire’s Mainstay Solutions chase the puck behind the nets at the 2013 New England Pond Hockey Classic on Lake Winnipesaukee.
Photo Credit : Kathie Fife Photography

Bay State Winter Games | January–Early March

Ranging in age from 5 to 70-plus, athletes from across New England will descend on the Berkshires for this annual sports spectacular, which marks its 35th anniversary in 2020 and hosts competitions in such winter staples as curling, figure skating, and masters ice hockey. Venues and dates vary by sport; see website for details. Various Berkshire locations, MA.

Newport Polar Bear Plunge | Jan. 1

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. Newport, RI.401-849-8048;

New England Pond Hockey Classic | Jan. 31–Feb. 2

Come celebrate the sport of hockey in perhaps its purest form, as pond hockey players from more than 40 states and six Canadian provinces travel to Lake Winnipesaukee to face off in a four-by-four round-robin tournament. Fans can take their pick of 500-plus games and enjoy an on-ice beer garden and evenings of live music, too. Meredith,

Jumpfest | Feb. 7–9

Once upon a time kids grew up impatient for winter, because they could climb their local ski jump and take off, soaring like birds. For a taste of this era, head to Satre Hill, where ski jumping dates back to 1926, for a weekend that includes the Eastern U.S. Ski Jumping Championships. Salisbury, CT.860-850-0080;

U.S. National Toboggan Championships | Feb. 7–9

Parents have been telling their progeny for ages that they’re the best sledders in the world; now the folks at the Camden Snow Bowl are challenging them to prove it. Daredevils of all ages will take to the historic Jack Williams Toboggan Chute to compete for the fastest time (and to sport zany and creative costumes). Camden, ME.207-236-3438;

Stowe Derby | Feb. 23

One of the oldest ski races in North America provides its participants—who range from National Ski Team members to recreational skiers—with the ultimate test of their abilities. The race begins atop Mount Mansfield and covers approximately 20 kilometers of challenging terrain before concluding at the Trapp Family Lodge. (As of 2019, the Stowe Derby also includes a fat-bike race over local trails). Stowe, VT.

Additional New England Winter Events for 2020


JAN. 4–5: HARTFORD,Connecticut Wedding & Bridal Expo. The largest event of its kind on the East Coast sets up shop at the Connecticut Convention Center to offer one-stop shopping for any and all wedding needs. 860-365-5678;

JAN. 16–19: UNCASVILLE,Hartford Boat Show at Mohegan Sun. The Earth Expo Center provides the venue for viewing all things boating, from luxury cruisers to accessories. 860-767-2645;

JAN. 17–19: EAST HADDAM,Festival of New Musicals. Emerging artists premiere musical works brought to life with the guidance and resources of the famed Goodspeed Opera House. 860-873-8668;

JAN. 17–19: HARTFORD,Hartford Symphony Orchestra: “The Four Seasons.” Ring in the new year—and the new decade—with Vivaldi’s evocative The Four Seasons at the Bushnell Center for the Performing Arts. 860-987-5900;

JAN. 23: STORRS,We Shall Overcome: A Celebration of Martin Luther King Jr.” The Jorgensen Center for the Arts hosts this living lineage of African-American music and culture that includes traditional and modern gospel, classical, jazz, Broadway, and spirituals. 860-486-4226;

JAN. 24–26: UNCASVILLE,The Sun Wine & Food Fest. Head to Mohegan Sun for a sprawling showcase of beer, wine, specialty spirits, and delectable dishes. Among the highlights are a grand tasting with 1,000-plus offerings and celebrity chef appearances by the likes of Rocco DiSpirito.

JAN. 26: RIDGEFIELD,“John O’Hurley: A Man with Standards.” As an actor, singer, and show host, Maine native John O’Hurley has done it all. Here he dazzles the Ridgefield Playhouse audience with storytelling, songs, and humor. 203-438-5795;

FEB. 20–23: HARTFORD,Flower & Garden Show. Spring arrives early at the Connecticut Convention Center, where more than 300 booths overflow with flowers, plants, herbs, bulbs, and seeds, not to mention informational sessions galore. 860-844-8461;


JAN. 1: OLD ORCHARD BEACH,Lobster Dip. One of the top fund-raisers for Maine Special Olympics, the Lobster Dip sees throngs of slightly nutty folks gathering at the Brunswick before taking a quick plunge into the Atlantic. 207-879-0489;

JAN. 10–12: AUGUSTA,Northeast Motorsports Expo. The Augusta Civic Center provides racing fans a terrific opportunity to meet drivers, get check out race cars, and talk shop with the experts.

JAN. 18–19: BANGOR,SnowCon. At the Cross Insurance Center, the focus is on board, card, and tabletop games, with ample opportunity to browse, play, and buy.

JAN. 26: ROCKLAND,Pies on Parade. Stroll among area restaurants and inns for samples of 50-plus kinds of pies, from sweet to savory. Be sure to buy your ticket early: This event sells out fast.

JAN. 31–FEB. 2: RANGELEY, Pond Hockey Festival. Celebrate a time-honored New England tradition at Haley Pond. There will be men’s and women’s divisions, with several age brackets as needed. 805-722-9172;

JAN. 31–FEB. 9: CAMDEN, Winterfest. This celebration of snow season begins with ice carving and snow sculpting and culminates with the U.S. National Toboggan Championships and fireworks.

FEB. 1: GREENVILLE,Wilderness Sled Dog Race. Since this race begins and ends right in town, you can cheer on the competitors from start to finish in one of only three long-distance races in New England (it’s a full 100 miles). 207-695-2421;

FEB. 15–16: PORTLAND,Maine Home & Remodeling Show. With more than 180 exhibitors and lots of expert-led seminars, Cross Insurance Arena has everything you need to shake off the winter blahs and start planning your next home and garden projects. 207-321-4246;

FEB. 16: SOUTH BRISTOL,Ice Harvest. Visit the Thompson Ice House to see how ice was harvested in days of yore. After watching the cutting and lending a hand with the transportation of the ice blocks, you’ll still have plenty of time for skating, wagon rides, and a visit to the museum.


JAN. 1: SOMERVILLE,Raising of the Grand Union Flag. To commemorate the American Revolution’s first flag raising, a processional led by a re-enactor portraying George Washington on horseback will leave from the City Hall Concourse at 11:30 a.m., followed by a ceremony at Prospect Hill Park. Attendees are invited to wear traditional colonial clothing.

JAN. 3–5: NEW BEDFORD,Moby-Dick Marathon. Join in the New Bedford Whaling Museum’s read-a-thon of one of America’s most enduring novels, Moby-Dick. The main event—the reading aloud of Herman Melville’s unabridged classic by local celebrities and volunteers—begins at noon Saturday. 508-997-0046;

JAN. 10–12: SPRINGFIELD,Boar’s Head Festival. Experience an ancient Epiphany processional celebration at Trinity United Methodist Church, complete with live animals. Purchase tickets in advance. 413-733-4759;

JAN. 16–19: WILLIAMSTOWN, I/O Festival of New Music. 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. 16–20: BOSTON,New England International Auto Show. Behold the premier showcase of newest-model vehicles, both imported and domestic, at the Boston Convention & Exhibition Center. 781-237-5333;

JAN. 25–26: WEST SPRINGFIELD,Railroad Hobby Show. Occupying several buildings at the Eastern States Expo, this is among the largest events of its kind. Real and model railroads are the stars, but you’ll also find art shows, a flea market, and more. 413-267-4555;

FEB. 7–9: HYANNIS,Boatbuilders Show on Cape Cod. “The best little boat show in the Northeast” returns to the Resort and Conference Center at Hyannis to give you a jump on the season, with plenty of accessories and beautifully crafted pleasure boats.

FEB. 7–9: SALEM,So Sweet Chocolate and Ice Sculpture Festival. This decadent fete brings ice sculptures, wine tastings, deals on Valentine’s gifts, and plenty of chocolate to downtown. 978-744-0004;

FEB. 21–23: 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. 508-823-0389;


ONGOING: LINCOLN,Ice Castles. At this frozen art installations/tourist attractions, caverns and slides and other fun formations are all carved from approximately 25,000 pounds of ice.

JAN. 17–FEB. 16: NEW CASTLE, Winter Wine Festival. Wine lovers won’t want to miss one of the signature events of the winter season at one of New Hampshire’s grandest hotels. Among the highlights: grand vintner’s dinners and champagne jazz brunches.

JAN. 24–26: 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. Note: While you can visit throughout the process, most pieces are not finished until Sunday.

FEB. 1: PORTSMOUTH, “The Lyin’ Kings.” 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. 6–9: HANOVER,Dartmouth Winter Carnival. Catch this raucous festival of garishly dressed Ivy Leaguers doing ridiculous things in the snow, plus polar bear swims, massive snow-sculpture contests, and races. 603-646-3399;

FEB. 8–9: 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. 12–16: NEWPORT, Newport Winter Carnival. Still going strong after more than 100 years, this townwide fete includes pancake breakfasts, a snowball tournament, parades and pageants, and fireworks.

FEB. 14–16: LACONIA, World Championship Sled Dog Race. Canine sled-pulling teams compete in races that start on Main Street and, depending on the category, go for either 6 or 16 miles. Who’ll be top dog?


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. 3–5: PROVIDENCE,Rhode Island Boat Show. This event at the Rhode Island Convention Center features hundreds of powerboats, sailboats, and more to get you fantasizing about summer.

JAN. 24–26: 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. 14–23: NEWPORT,Winter Festival. This annual extravaganza includes activities throughout the city that offer fine food, music, and entertainment for the whole family. 401-847-7666;

FEB. 14–23: PROVIDENCE,Children’s Film Festival. A variety of downtown venues will screen indie films geared toward ages 3–18. Workshops for kids and a young filmmakers showcase round out the festival. 401-209-7585;

FEB. 22: WOONSOCKET,Mardi Gras Celebration. Honoring the area’s proud French-Canadian heritage, the festivities at St. Ann Arts and Cultural Center include live music and a Cajun-inspired dinner.


JAN. 18: QUECHEE, Winter Wildlife Celebration. Visit the Vermont Institute of Natural Science (VINS), the home of many winged ambassadors for this day that’s all about family fun. 802-359-5000;

JAN. 23–26: 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. 25–26: BRATTLEBORO,Northern Roots Traditional Music Festival. Performers representing the best northern musical traditions come together for a day of workshops, panels, and mini concerts at New England Youth Theater and McNeill’s Brewery. 802-257-4523;

JAN. 28–30: ESSEX JUNCTION,Vermont Farm Show. The Champlain Valley Expo Center plays host to this annual event, which features more than 250 booths showcasing everything from beekeeping to sugar making to dairy farming. 802-878-5545;

FEB. 1–2: CRAFTSBURY COMMON,Craftsbury Marathon Doubleheader. At the largest Nordic ski event in the East, you can register for the classic marathon on Saturday, skiing either 25 or 50 km, or opt for the slightly shorter freestyle marathon on Sunday. Or do both! 802-586-7767;

FEB. 8: BURLINGTON,Brrrlington Winter Bash. The Miller Recreation Center hosts a free day of family activities, from dogsled races and snow fort building to crafts and food. 802-540-1058;

FEB. 15–16: BRATTLEBORO,Fred Harris Memorial Tournament. Ski jumping returns to Harris Hill for a winter spectacle that 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.