16 New England winter getaways

Outside view of Stowe Mountain Resort with hockey rink and Whistling Pig

New England during the winter is whimsical. With its quaint towns, snowy landscapes, and winter festivities, there is plenty of fun to be had. With most destinations situated relatively close together, a family road trip is a great way to experience it all. Find out our favorite New England destinations — which will appeal to skiers and non-skiers alike — in our guide to the best New England winter getaways.

Outside view of Stowe Vermont

1. Stowe, Vermont

Anyone who has visited Stowe in the winter is immediately captivated by its charm. A slow drive along its quaint Main Street, lined with cozy cafes, inviting boutique shops, sparkling lights, and warm restaurants, never fails to leave visitors in awe. If you’re a skier, don’t miss an afternoon on the snowy slopes at Stowe Mountain Resort, just a short drive from town. Non-skiers can take a sleigh ride through its peaceful, powdery landscape, go snowshoeing in the nearby trails, or snowmobile through the forest.

When you’re ready to dine, head to The Bench or The Roost, whose menus include a variety of meals for the whole family to enjoy. Kids will love a chance to build their own snow sculptures while parents enjoy a locally crafted beer or an evening massage. with all the wintry things to do in Stowe, VT, it’s one of our most highly recommended New England winter destinations for a road trip.

2. Newport, Rhode Island

Newport is an ideal New England winter getaway for non-skiers for its rich history and breathtaking views. Take the family for a memorable stroll along the Cliff Walk trail, located right on the coast. From here, warm up on a tour through the opulent, Gilded Age mansions that Newport is renowned for: The Breakers and the Marble House. 

After a day of exploration with the family, treat yourselves to a delicious meal at The Mooring or The Black Pearl, both known for fresh, local seafood. A walk through downtown Newport is a wonderful way to round out your evening before hitting the road in the morning to visit your next destination together.

3. Boston, Massachusetts

Boston comes alive when the temperatures drop, hosting dozens of exciting festivals and seasonal events for everyone in your family. Lace up your skates for a glide across the ice at Frog Pond in Boston Common to get into the winter spirit. For history buffs, the historical landmarks along the Freedom Trail are a must-see on your winter road trip itinerary.

Interested in some day trips in New England in the winter? A rental van offers the chance to visit Cambridge, home to Harvard University, and spooky Salem, known for the famous witch trials. You’re probably hungry by now, and Boston offers everything from seafood at Legal Sea Foods to Italian cuisine in the North End.

4. Portsmouth, New Hampshire

Portsmouth’s beautiful downtown is brimming with eclectic shops, galleries, and restaurants, making it a vibrant stop on a New England winter getaway for non-skiers. Enjoy a family stroll through the streets, adorned with festive decorations during the holiday season.

If you’re feeling active, head to the ice skating rink at Strawbery Banke Museum or catch a show at the Seacoast Repertory Theatre. Load the family in the warm, cozy van for a scenic drive to New Castle, a darling island town with sweeping views of the Atlantic Ocean. 

Heard enough? Let us help you plan your Portsmouth road trip!

Source: Back Road Ramblers

5. Bar Harbor, Maine

Looking for classic New England ski resorts? The picturesque village of Bar Harbor offers a picture-perfect winter landscape of white mountains and icy shores. If you and your family love the outdoors, bundle up for some cross-country skiing, snowshoeing, and wildlife watching in Acadia National Park, a must-see on your New England winter getaway and just a short drive away!

After a day in the snow, warm up with a meal together at The Thirsty Whale or Side Street Cafe. We also recommend the 30 minute drive south to see Bass Harbor Head Lighthouse and its coastline views.

6. Woodstock, Vermont

Quaint and historic, Woodstock is an ideal place to experience a New England winter. It’s a great winter getaway for both skiers and non-skiers, so whoever wants to hit the slopes can head to the mountains while the others head to Woodstock Nordic Center for a day of sledding and snowshoeing. 

The town hosts a variety of family-friendly winter festivities, like its famous Woodstock Wassail Weekend. Hungry? The whole family will enjoy hearty, farm-to-table meals at The Prince & The Pauper or comfort food at Worthy Kitchen.

Source: Woodstock Inn

7. North Conway, New Hampshire

Some of the best New England ski resorts can be found in North Conway. You and the family can spend the day skiing or snowboarding together at Cranmore Mountain Resort, or in the iconic White Mountains for snowshoeing and ice climbing.

Don’t miss this classic New England day trip in the winter: head out for a scenic drive to Mount Washington Valley, whose mesmerizing natural beauty will impress even the pickiest of travelers.

8. Kennebunkport, Maine

This lovely coastal town brightens up during the holiday season, with streets and shops graced with sparkling lights. Take the family out for an evening together at Dock Square, the heart of Kennebunkport which explodes with unique boutiques, art galleries, and restaurants. 

It wouldn’t be a proper winter getaway without an afternoon of ice skating at the Waterhouse Center. When hunger hits, there are options for kids and adults alike, from seafood at The Clam Shack to fine dining at Earth at Hidden Pond. Take advantage of your rental van with a must-do New England day trip in the winter to Cape Porpoise Pier. The views of the harbor are worth it.

9. Providence, Rhode Island

Providence is an excellent New England winter getaway for non-skiers and active families. Layer up and hit the ice at the BankNewport City Center for a fun afternoon of winter activity.

Art-loving families will especially enjoy Providence, as it’s home to the Rhode Island School of Design Museum and the Providence Children’s Museum. Be sure to check out WaterFire, a unique art installation that lights up the rivers downtown. When it comes to dining, Providence has something for everyone, from Italian cuisine in Federal Hill to farm-to-table dishes in Downcity.

Source: RI Monthly

10. Mystic, Connecticut

A New England winter getaway would not be complete without a visit to the enchanting Mystic Seaport, home to the largest maritime museum in the United States. Kids will love the Lantern Light Tours: an outdoor, self-guided experience showcasing how holiday celebrations have evolved from past to present. Take advantage of Mystic’s proximity to these well-known lighthouses in New England by hopping in the van for a day trip to visit them.

Have you seen Mystic Pizza? Why not download the movie for passengers to watch while on the road to Mystic. Then, surprise the kids with dinner at the real-life Mystic Pizza! 

11. Montpelier, Vermont

It might be the smallest state capital in the country, but that doesn’t mean Montpelier isn’t bursting with life! Take the family ice skating at Central Vermont Memorial Civic Center or head to Hubbard Park’s long, gentle slopes for sledding. 

Once you’ve worked up an appetite, try The Bagel Cafe for delicious sandwiches, soups, and of course, fresh bagels. Then, check out the Vermont State House and its free guided tours of the gold domed capitol building. The views of Montpelier and the surrounding mountains from the top of the dome are spectacular.

12. Burlington, Vermont

Burlington is one of New England’s most vibrant winter destinations. The city hosts several winter festivals, including Vermont Brewers Festival and the Burlington Winter Carnival which includes ice sculpting, snowshoe races, and a parade. The Waterfront Park features an outdoor ice skating rink with panoramic views of Lake Champlain.

There is a great bike path along the Waterfront that the kids are sure to love. Adults, on the other hand, can indulge in some shopping at Church Street Marketplace and dining at Zero Gravity Brewpub or Switchback Brewing Company. A visit to the Shelburne Museum won’t disappoint, and its 45-acre grounds are especially captivating during the winter months.

Source: BRB Travel Blog

13. Camden, Maine

Camden is a must on your road trip exploring the best of New England’s ski resorts, as the crown jewel is the Camden Snow Bowl, a ski area nestled in the mountains overlooking Penobscot Bay. If you’re a family of sports lovers, this is your chance to go downhill and cross-country skiing, snowboarding, and tubing together. Non-skiers, in the meantime, can enjoy Harbor Park and its gorgeous views of both the coastline and the snowy islands of Penobscot Bay. 

February’s Winterfest celebration shouldn’t be missed! There will be ice sculpting, snowshoe races, a chili cook-off, live music, and other family-friendly activities. Looking for a nature break? Pile into the van for a short but beautiful drive to Coastal Mountains Nature Trail and Camden Hills State Park, the perfect New England day trip in the winter.

14. Lincoln, New Hampshire

Lincoln’s wintry landscape will captivate you. Skiers will revel in Loon Mountain, a premier ski resort nestled in the heart of the majestic White Mountains. Non-skiers should not miss an afternoon at The Ice Castles, where magical ice formations with intricately carved tunnels, slides, and towers are sure to impress. We highly recommend a visit to Flume Gorge, a narrow granite canyon with cascading waterfalls and scenic trails. It’s a short drive from town and easily accessible by van.

Hungry? Lincoln offers lots of wonderful places to snuggle in for a family meal. There are cozy pubs, family-friendly restaurants, and upscale dining with menus to suit every taste. Leave feeling stuffed, happy and full of love.

15. Bretton Woods, New Hampshire

Nestled in the White Mountains, Bretton Woods is home to the state’s largest ski area, As a top-notch New England ski resort, you will adore its pristine slopes that offer excellent skiing, snowboarding, and magical sleigh rides through the snowy landscape with the whole family.

Fancy an adrenaline rush? Bretton Woods Canopy Tour hosts a thrilling zip-lining experience through the treetops. This is a wonderful memory to make as a family! Take a van ride to the majestic Mount Washington Hotel and its unparalleled views of Mount Washington, the highest peak in the Northeastern United States.

16. Chatham, Massachusetts

If you’re seeking a New England winter getaway without the snow, head to Chatham on Cape Cod. The lovely Main Street is lined with quaint shops and snuggly cafes, where you can warm up with a hot cup of cocoa together. If you’re a family that loves animals, don’t skip the short drive to Monomoy National Wildlife Refuge. 

Speaking of short drives, the iconic Chatham Lighthouse, standing tall against the coastal backdrop, is worth a trip. History lovers will want to make a stop at the Atwood Museum for a fascinating glimpse into Chatham’s past. 

Explore these New England winter destinations in style 

The best way to experience all that New England has to offer is through an exciting road trip with your loved ones. Here are some tips to ensure a smooth and easy winter adventure!

What to pack for your New England adventure

For your New England adventure in the winter, you should pack warm jackets, boots, gloves, hats, long johns, and skis if you plan on skiing. Does lugging all of that to the airport sound exhausting? Renting a van affords you the space you need to bring all your gear, plus cozy extras like blankets, snacks, and pillows for the ride.

Map your ideal route

When mapping your ideal route for your New England winter road trip, consider road conditions and plan scenic stops along the way. Bring along this list of must-see destinations, and prioritize your stops according to the time you have available to explore with your family. Google Maps and Waze are great apps to assist with daily planning, as each will provide warning of road closures or accidents to avoid. 

Talk about the activities that are most important to everyone coming along for the ride through New England’s winter wonderland. If you’re a family of skiers, prioritize destinations like Stowe and Lincoln. If you’re more interested in landscapes and history, destinations like Newport and Chatham will be far more appealing.

Get the right vehicle

Going on a New England winter road trip is truly an unforgettable experience, made better by traveling together in one vehicle. We want to help you turn this idea into a reality by providing comfortable, safe transportation to every stop on the list! We know that the more space you have to relax on the road, the happier everyone will be.

Whether you’re skiing or not, it’s best to maximize the room you have while traveling. More than that, the vehicle for your winter road trip should offer comfort, heating, and winter driving features. This ensures that you’ll spend less time fretting about details and more time talking, laughing, and reminiscing!

Maximize winter whimsy with Greenvans

A spacious van, like those offered by Greenvans, is a great option for a New England vacation in the winter since its fleet is tailored for comfortable and safe winter road trips through any type of weather. Our vans come equipped with heating, cargo space for skis and sleds, and winter-ready tires.

And with offices all over the Northeast U.S., including Providence and Boston, picking up your family van puts you exactly where you need to be. As you can see we like to make things easy, so your cozy family vacation can be all play and no work.


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