things to do in winter in Maine

8 Fun Things to Do in Winter in Maine

Though it may come as a surprise, there are nearly endless things to do in winter in Maine! It may be a bit chillier than our iconic summers, yes, but there is no shortage of fun to be had. With the freedom of retirement, each day serves as a new opportunity to pursue the activities you love (and even try some new hobbies)! To make the most of winter in Vacationland, keep reading for some of our favorite local activities.

1. Pineland Farms

The property at Pineland Farms in New Gloucester is pristine any time of year, but it has a little extra magic during the winter when there is a crisp white layer of snow covering the grounds. Not only is it beautiful to look at, it’s very fun to cross-country ski! Their groomed trails span more than 30 miles and equipment rentals are available if you don’t have your own. Grab a pastry and a hot drink at the Pineland Market on your way out, and you’ve got the perfect Maine winter activity!

2. Bradbury Mountain

If you’re looking for a lovely winter hike, Bradbury Mountain is just the ticket! Though it’s a smaller, less-challenging hike, you will still get amazing snow-capped views from the peak – and will likely have the trails all to yourself. Just be sure to take normal winter hiking precautions, such as knowing your route, being mindful of the weather, hiking in daytime only, and investing in some shoe spikes to help prevent slipping on the ice.

3. Maine College of Art Classes

Looking to learn a new artistic hobby or hone your current skills? The Continuing Studies Department at Maine College of Art & Design offers open-enrollment art programs to adults all year long! They have a selection of different types of weekly classes, both winter and summer intensive sessions, and even international artist retreats. You are sure to find a program you love at MECA!

4. Twin Brook Recreation Area

Twin Brook Recreation in Cumberland is a sprawling preservation that is somehow even more picturesque in winter, and you will always feel like you have it to yourself! The two-mile loop trail takes you along a bubbling river, perfect for walking (they are dog-friendly, so bring your pup along!), snowshoeing or cross-country skiing. There’s also plenty of parking and restrooms are easily accessible. Plus, it’s right down the road from us at Cumberland Crossing!

5. Oxford Casino

Oxford Casino offers various gaming opportunities for whatever you may be in the mood for – from table games to slots. To sweeten the pot, every Wednesday at Oxford Casino is Senior Day, with exciting prizes to be won. They even have a rewards club!

6. Chebeague & Cumberland Land Trust

The Chebeague & Cumberland Land Trust boasts hundreds of acres of stunning 

outdoor space, ranging from forest trails to farmland, making it an idyllic setting for snowshoeing, cross-country skiing or taking a wintertime walk. Exploring this state-protected land is the ideal way to spend a snowy winter day!  

7. Downhill Skiing

This winter, take a Maine downhill ski trip to any of our several beautiful snow-capped mountains! Whether you’re in the market for the challenging runs of Sugarloaf or leaning towards a more easy-paced experience at Shawnee Peak, there is something for everyone. The best part is that all of our most popular skiable mountains are just short drives from Cumberland Crossing’s campus!

8. Walk the Eastern Trail

The Eastern Trail, which stretches from Kittery to South Portland, is a 65-mile trail (including 22 off-road miles) that takes you through forests and marshes, over bridges and past lighthouses. The trial is open year-round to walkers, runners and bicyclists, making it a great way to get outside without worrying about traffic! 

Cumberland Crossing by OceanView

Cumberland Crossing by OceanView is an independent living community centrally located in Southern Maine. For a breathtaking, stress-free place to call home that is easily accessible to so many of the wonderful activities Maine has to offer, look no farther than our community! Let us help you enjoy the hard-earned gift of retirement to the fullest extent. Contact us today to learn more!