Our Favorite Winter Getaways

January 8, 2016

Last year’s winter has lots of New Englanders dreading those freezing, blustery winter days—and rightfully so. But I’ve got a proposition: Let’s not forget the romance of the season and, as tempting as it is, let’s not just binge on netflix at home until it passes. Let’s get out of the house and explore, enjoy a nice meal that we didn’t cook, and relax with a cocktail that we didn’t mix. For the brave souls out there, ND’s contributors have pulled together a menu of winter getaway options that are just a drive from the North Shore.


GO: North Conway, NH. Some people wait all year to experience the White Mountains in the winter. Why not become one of them?  Even if you are not a skier, there is still plenty to see and do in North Conway.  So bust  out those snow pants and enjoy a snowy weekend trip.

DO: Sleigh ride at Farm By the River. Hot chocolate and extra blankets keep you warm on this thiry-five minute picturesque ride in the snow. Bring your bathings suits and hit up the Kahuna Laguna indoor water park. And, of course, check out the long list of winter-related outdoor activites at Cranmore Mountain.  During nap time, turn on your seat warmer, put on some mellow music, and take a long drive to enjoy the scenery.

EAT:  Pick up a coffee or choose from a long list of decedant hot chocolate and baked goods at The Met.  Eat lunch at Delaney’s Hole in the Wall which offers hearty affordable food and an atmosphere so lively that no one will take notice of ill-behaved children. My kids loved the decor at May Kelly’s Irish pub. (Bonus: Whipped-cream-topped hoodsie cup are an included with the kids meal.) Flat Bread Pizza always has fantastic pies. Don’t skip the brownie sundae.

STAY: When traveling with the entire family, I always opt for a home rental. Sharing a hotel room with toddlers in the winter is my idea of torture. There are tons of affordable rental options here.  I would pick something close to town (traffic can be an issue) and with a fireplace—nothing says White Mountains like a roaring fire and a hot toddy at day’s end.

GO: Boston, MA.  Winter equals museum season for the parents of young children, and with so many museums to choose from in Boston, a day or weekend trip is a great way to stay active when you can’t get outside.  I highly recommend taking the train into town. Bundle up, bring a thermos full of hot chocolate, and it is like the Polar Express all over again.  The video below is a day trip we took in April, right after the snow melted (yes, winter is that long).

DO: Listen to the Boston Youth Symphony Orchestra. Visit the New England Aquarium or the Children’s Museum. Be smart and call your local library ahead of time to reserve reduce rate museum passes.

EAT: If you’re visiting the Children’s Museum, don’t miss the nearby Flour BakeryFaneuil Hall is always a win. Let the kids stroll the shop-lined halls, pick their favorite meal, and choose a spot to eat in the rotunda. The Prudential Center also has kid-friendly chain restaurants, a food court, and plenty of indoor space to run around.

STAY: Marriot’s Custom House is close to both the train and the aquarium. Waterfront suites and villas are great for a family and provide lots of room to spread out.  (The only negative there? No indoor pool.)  The Westin Copley, on the other hand, boasts and indoor pool, welcome gifts for kids, and a prime location: attached to the Prudential Center.



GO: Portland, ME. Portland has a pretty active night life, and business owners there have learned to build comfortable spaces for people who, for at least five months out of the calendar year, are wicked cold. The list below includes some of NDT’s favorite cozy spots that vary in vibe, price-range, and location.

*NOTE: The city of Portland is situated on a peninsula that’s about two miles long from the East End to the West End, which makes it easy from hop to place to place. We’ve ordered the locations in each section from East to West, which may make it easier to plan your night.


DO: Relax at Soakology, and even indulge with a chai tea and chocolate. Check out live music at The State Theatre or Port City Music Hall.  Get lost in Yes Books on Congress Street.

Kenya Hall at Port City Music Hall

EAT: Start with a pre-dinner cocktail at Lolita, Hunt & Alpine ClubSonny’s or The Bearded Lady’s Jewel Box. Try dinner at Roustabout, Honey Paw, Evo, or Pai Men. Finish with a nightcap at MapsNovare Res, LFK, or Bramhall.  Don’t leave in the morning without picking up a heavenly dozen at The Holy Donut.


STAY: Who doesn’t love the Westin’s heavenly bed? In addition to the duvet charm, some of the best customer service I ever received was during a stay at the Westin Portland Harborview.  Have a drink at the Top of The East, the rehabbed rooftop bar, with a stunning view of the city. The decor is decidely not New England, but the drinks and scenery are fantastic.


GO: Wentworth By The Sea in New Castle, NH

DO:  Arrive and have a drink in the lounge. Take a swim in the indoor pool and watch the snow fall from the outdoor hot tub. Bundle up and walk around New Castle. Relax at the spa. You really could stay the entire day at the grand hotel, but if boredom sets in, take the quick drive to downtown Portsmouth.

EAT: The in-hotel restaurant, Salt, never disappoints.


GO: White Mountains, NH (North Conway and surrounding areas)


DO: Strap on your snowshoes and venture up Mount Washington. Don’t worry, this hike may be challenging but it’s more manageable than you think. Go mid-morning for optimum daylight and take the Tuckerman Ravine Trail. Hike up to the Caretakers Cabin, you will pass skiers hiking up in skins, warming up at the base of the ravine (which is where you pivot to head back down the trail). Round trip, it’s about three hours. You could also do this without snowshoes if your winter boots are rugged enough.

Cranmore is one of the easier skiing mountains in the area, but it’s a decent size and fast lift lines keep it fun. It’s also located in the center of North Conway and tickets are reasonable—often you can get a deal. It’s super kid-friendly, so beware for little tikes buzzing by you. For a more challenging (and bitterly cold) mountain, check out Black Mountain in Jackson, NH—about a 30-minute drive from North Conway.

Great Glen Trails is a bit of a hidden gem. Here, you can cross-country ski, snowshoe, tube, and take the SnowCoach up Mt. Washington. Nothing beats the aerobic workout of a cross-country ski! Opt for the classic cross-country skis if you’re a beginner, and when you take a break from skiing, hit up the tubing hill. On Mondays and Fridays, their fees are two-for-one, which is a great deal if you’re renting skis and getting a half-day pass. Warm up in the lodge with some hot cocoa after you explore!


EAT: Breakfast at Peaches is the best in town. It feels like breakfast in your grandma’s living room (in a good way) and they offer a plethora of savory and sweet options. Lunch or dinner at Moat Mountain Brewing Co is a must. It’s not at all fancy, more of a smoke house meets sports bar, but the menu has something for everyone and it’s the best pub food in the area. Go for the Nachos after a day of skiing and don’t be afraid to sample the jalapeno cornbread or Thai peanut soup.

STAY: You have your run of the gamut when it comes to places to stay in these parts. You can go high-end—there are B&Bs galore—or you can find a room in one of a major hotel chains if you’re looking to use up some points. On the (relatively) cheap, you can stay at the Hampton Inn and Suites in North Conway. It’s centrally located, it’s new and clean, and it has a pool, gym, hot tub, and free breakfast.

So go, do, explore!

xoxo ND

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