maine weekend getaways

4 Maine Weekend Getaways to Experience This Winter

Winter in Maine means a few things: chillier weather, unique outdoor activities, and no touristy crowds! This means there is no better time to plan your perfect weekend adventure. There are so many activities to enjoy this season; for those of us lucky to already live in Maine, booking a “staycation” allows you to take advantage of all our beautiful state has to offer. And if you don’t live in Maine yet, now is the time to choose your site at Cumberland Crossing and fall in love with winter in Vacationland next year with one of these four Maine weekend getaways!


While Rangeley is notorious for being stunning throughout the fall season, it simply can’t be beat in the winter! For the winter activity lover, there are nearly endless options for you to enjoy the season. Hit the ski slopes at nearby Saddleback Mountain or Sugarloaf for exhilarating downhill skiing or check out cross-country ski trails around the Rangeley Lakes Trail Center. You can even book huts through Maine Huts & Trails where you can stay overnight along your journey!


Kennebunkport is truly an all-seasons destination, with plenty of activities to enjoy throughout the year. Explore miles of nature trails on snowshoes or cross-country skis, bundle up for a horse-drawn sleigh ride through town, or simply go for a staycation in one of the many romantic inns located within walking distance of the rocky shoreline. The pristine beauty of seaside Kennebunkport is a can’t miss weekend getaway!


Camden, and really all towns along Maine’s Midcoast, are an obvious choice for a summer weekend, but you may be surprised at the beauty and fun they bring in the winter! In Camden, you’ll experience everything from ice sculpting and the U.S. National Toboggan Championships to skiing at the Camden Snow Bowl overlooking the Atlantic. Looking for a more relaxed weekend? Take in the sights and shops as you walk through the snowy streets of town. 


Offering a vibrant experience all through the year, Belfast boasts a variety of arts-based attractions to get you through the winter. The aptly named Cold Comfort Theatre offers musicals and comedy shows, while the Waterfall Arts community center allows you to appreciate contemporary work, as well as access to workshops and classes. Many of the town’s restaurants are open year-round, so you can fill your belly with delicious seafood after a long day of indulging in the local arts! Of course, for all staycation ideas, call ahead for current Covid restrictions.

Cumberland Crossing by OceanView is an active senior retirement community, centrally located in Cumberland, Maine. This means there are plenty of fun Maine weekend getaways for you to enjoy when you move to our community! To learn more about Cumberland Crossing, please contact us today!