Friday
Head for the hills

Whether you’re a diehard skier looking to carve up the slopes or a winter vacationer in search of a change of scenery, you can’t go wrong with a weekend in the western mountains of Maine. As you make the trek up to Carrabassett Valley (driving slowly, as afternoon snowstorms are the norm in the Pine Tree State), there are a few key stops along the way that will help you get into the mountain mindset. Make sure to visit Douin’s Market and Diner in New Sharon for a signature brownie whoopie pie, and if you are in need of any extra reading material for cozy evenings next to the fire, a stop for used books at Twice Sold Tales in Farmington is a must. As you near your destination and home for the weekend, get your fill of caffeine at Carrabassett Coffee Company in Kingfield. It’s a small-batch specialty roaster where you can choose from a variety of freshly roasted coffees to sustain you during your 48-hour jaunt away from your home coffee setup. Feeling a little peckish after the long drive? Grab a burrito from favored local haunt Rolling Fatties, where unexpected ingredients like falafel and dill pickles pack a surprising and delightful punch. If you’re looking to mostly eat in for the weekend, stock up on groceries and necessities at Mainely Provisions, and then browse the impressive selection of IPAs, pilsners, saisons, and more at The Maine Beer Shed, which carries both craft beer and farm products from across the state.

A visit to Carrabassett Valley almost always guarantees spending time on skis. Booking a room at the Sugarloaf Inn, conveniently located at the base of the ski resort, allows for quick and easy access to the hill. Splurge a little—you’re in the land of mountain chalets, after all—and settle into a deluxe suite with a lounge, private balcony, mountainside views, and a dangerously comfortable king-size bed. Once you’ve stored your ski equipment in the hotel’s locker room, head into the village for some mountain ambiance. A visit to wine bar Alice and Lulu’s is a great start to the après-ski scene; you can grab light appetizers and a glass of cabernet or sauvignon blanc to whet your appetite. Next, have dinner at Hug’s Italian Restaurant, where classic Italian fare will warm you up enough to brave the walk back to the hotel before you turn in for the night.

Saturday
Hit the slopes

Keeping an eye on the weather forecast, get breakfast at Shipyard Brew Haus, a day-to-night restaurant attached to the Sugarloaf Inn with quick access to the Sawduster chairlift, which will deposit you at the base of the mountain. If you’re still feeling sluggish or there’s a wind hold on the lifts delaying the opening of the upper mountain, find a quick cup of coffee at Java Joe’s to wake yourself up. On the slopes, sticking closer to the lower mountain will provide plenty of opportunities for beginners to get comfortable on two planks, while hopping on the Skyline lift will be more appealing to seasoned shredders. Looking to get away from the crowds? It’s a bit of a trek, but heading over to the less trafficked, far eastern side of the mountain via the King Pine lift guarantees numerous laps and short lift lines for expert skiers.

If you’re not a bell-to-bell winter athlete, head in early to take advantage of the various activities in the village. Grab a quick lunch of soup and a sandwich at D’Ellies Bakery and Deli, fuel up quickly with a delectable meal from Black Diamond Burritos, or skip straight to dessert and warm up with a round of hot and fresh doughnuts from local favorite Eighty 8 Donuts. Try whimsical pastries like the Bamm Bamm, topped with Fruity Pebbles cereal, or the Ol’ Blue Eyes, featuring lavender glaze, lemon curd, and Nilla crumble. Now it’s time to relax; peel off your snow pants, pull on your swimsuit, and book it over to the Sugarloaf Sports and Fitness Center. Bask in the hot tubs until you’re adequately loosened up, and then take a quick dip into the pool to cool off. If you’re looking to really unwind, consider calling ahead to book an hourlong massage (Swedish or deep tissue, your choice) to get all the knots out before you rush off to your dinner reservation.

A trip to Sugarloaf is incomplete without at least one meal at The Bag and Kettle, a favorite among locals, newcomers, and Sugarloaf devotees alike. It’s known for the famous Bag Burger and legendary après-ski amusements. If you’re looking to fully enmesh yourself in ski-bum culture and the Sugarloaf community, and you’re hoping to catch sight of a shot ski (four to six shot glasses screwed onto a ski for group imbibing), the Bag is your go-to restaurant. If you’re in the mood for a quieter, more romantic dinner, the Coplin Dinner House in Stratton is a 15-minute drive from the base of the resort. With a fine dining menu that changes daily and focuses on local ingredients, you’re sure to tuck into a meal you’ll remember for months to come.

Sunday
The dog days of winter

Not a skier but still want to get out into the winter wonderland? Consider booking a ride with Dogsled Maine, a family-run kennel of sled racing dogs living out their retirement doing what they do best: running fast. A chorus of joyful howls will serenade you as you whip around wooded trails and see the mountain from an entirely different perspective while bundled up warmly in numerous blankets. If you’re traveling with little ones who tire quickly in the snow, a trip to the Sugarbowl Family Entertainment Center might be in order. Hit up the lanes for a couple of rousing bowling matches, or if you’re feeling nostalgic for summer, try your hand at virtual golf! With options to play 18 rounds at any golf resort in the country (minus the walking and sun in your eyes), you can practice your driving and putting without breaking a sweat. If you’re visiting Carrabassett Valley closer to fall or spring, your options for other outdoor activities might be expanded. If you love two wheels as much as you love two planks, be sure to check out Freeman Ridge Bike Park, which offers over five miles of single-track mountain bike trails, or the 80 miles of trails developed and maintained by the Carrabassett Region Chapter of the New England Mountain Bike Association that run throughout the entire valley. Regardless of how you choose to spend your mountain weekend (whether on the slopes from dawn to dusk or enjoying plenty of downtime in the lodge with a cup of hot cocoa), you’re sure to be plotting your next mountain excursion before you even pack up your gear and head back to sea level.

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