10 Amazing Winter Day Trips From Portland Maine

Portland Maine charms visitors year-round with its cobblestone streets, vibrant arts scene, and fresh seafood. But when winter’s icy grip arrives, a different kind of magic takes hold. Snow blankets the quaint city and rugged coastline, transforming them into enchanting winter wonderlands.

When you want to leave the big city and explore more Maine winter wonders, you don’t have to drive too far. Plus, this is Maine, where the residents are skilled at clearing snow-covered roads quickly.

Here are the best winter day trips from Portland that are less than three hours, taking you from the slopes to beaches by the sea.

Kennebunkport & Kennebunk

A 30-minute drive perfect for those who want seaside views, seafood, and shopping.

This easy ride down I-95 can be exchanged for the scenic route through Saco and Biddeford. Stop by Fortune Rocks Beach or Goose Rocks Beach to search for sea glass. You’ll pass through the village of Cape Porpoise, a working fishing village with one of the newest restaurants in The Kennbunks — Ultramar Restaurant.

The scenic road brings you right to the heart of Dock Square, which shares a border with Kennebunk and Kennebunkport. This idyllic, sophisticated iteration of a fishing village doesn’t shutter the windows every winter, and staples like Alisson’s Restaurant still serve some of the best lobster rolls and bowls of chowder you’ll ever taste.

Across the Kennebunk River, Kennebunk has three beaches, plus the Lower Village and Historic Main Street downtown to explore.

Bath Maine

About a 40-minute drive perfect for those intrigued by the history of maritime history, shipbuilding, and historic towns perfectly preserved.

Big things happen in Bath, a shipbuilding community backed by a downtown village that reminds you of a bygone era. Try to time your trip for the annual Winterfest, usually held in mid-February.

As the “City of Ships,” the Maine Maritime Museum is a must-see. It is open all winter with scheduled events and evolving exhibits.

Add an extra 30 minutes to your trip and head for the mouth of the Kennebec River at the fabulous Popham Beach State Park.

Ogunquit Maine

A 45-minute drive ideal for couples or those who want endless beach walks in winter.

Ogunquit brings a comfortable charm to its seaside community and quickly rose as one of the top inclusive destinations in New England. This diverse community captures the artistic essence of the Maine coastline with its downtown area and Perkins Cove offering unique experiences within walking distance.

Nearby, you have almost 4 miles of pristine beach and the Marginal Way cliffside walk open as weather allows (bring spikes for your shoes). Plus, several resorts here are adults-only, making Ogunquit a perfect place for a romantic getaway.

Sebago Lake

A 1-hour drive perfect for those who don’t have the patience or time to drive to the larger, more distant lakes.

You know a lake has to be pretty spectacular when it’s where the locals go. Sebago Lake is one of the favorite getaways for Portlanders, and it’s just a quick drive on Route 302 to Sebago Lake State Park. The park is split between Casco and Naples, with nearly a dozen miles of winter trails to explore via snowshoeing or cross-country skiing.

In the summer, finding a campsite here is almost impossible because of demand. But, winter camping is always available. And for those feeling REALLY adventurous, take the 30-mile Sebago to the Sea Trail, which brings you right back to Portland.

Bridgton Maine

A 1-hour, 15-minute drive for people who love night skiing — it’s one of the only places you can do so in Maine.

Another 20 miles past Sebago Lake, Bridgton Maine is home to Pleasant Mountain Ski Area. Nearly half of the trails are lit at night, and special events are planned all winter long.

This is another community that celebrates what winter brings and doesn’t hide from it. Look for the annual Maine Lakes Winter Carnival schedule each February.

Plus, Bridgton is home to the highest point in Southern Maine with snowshoeing, cross-country skiing, and snowmobile trails available. Please note that Pleasant Mountain hikes are part of the Loon Echo Land Trust and a separate entity from the ski resort.

Bethel & Sunday River

A 1.5-hour drive perfect for diverse groups who want a little bit of everything Maine winters have to offer.

Somehow, the charming town of Bethel and the shenanigans of the Sunday River team blend perfectly in this outdoor adventure region that shows an amazing side in winter. Bethel shines with a mix of Charles Dickens and Norman Rockwell, with people as welcoming as the landscape.

Just up the road about 6 miles, Sunday River is a four-season feast of fun. The ski resort just keeps coming up with new and innovative ways to keep the party going. With eight peaks, it gets serious when it comes to riding the slopes. Whether you just want a drink or need to tackle Black Diamond runs, it’s all there with a barrel of laughs at Sunday River.

To get a taste of their personality, check out Olympian Donny Pelletier on Facebook or your favorite social site.

Camden Maine

A 1.5-hour drive perfect for every human being on the planet — skiing, hiking, shopping, dining, views, architecture, and history abound.

Camden shines in all seasons, but the opening of winter’s Camden Snow Bowl, in addition to the Camden Hills State Park views, just adds a snowball on top. You won’t find another ski area in the state with these ocean views. And every February, the National Toboggan Championship takes over the Camden Snow Bowl.

Downtown Camden wraps around the harbor, offering shops, dining, and exploration through piers and parks. If you take Route 1 to get there, you’ll get the bonus of Rockland and Rockport on the way. Definitely plan a stop at the Rockland Breakwater Lighthouse, and if the movie “Andre” touched your heart as a youngster, his real-life story happened in Rockport where a statue honors the famous seal.

Bangor Maine

A 2-hour drive perfect for Stephen King fans or those who appreciate a bigger city that hasn’t gone too commercial.

Bangor might be Maine’s Queen City, but it’s as much about a King – Stephen King – on top of that.

Visit the gates of Stephen King’s former home and look for the different locations that inspired famous horror stories like “It” and “Pet Sematary.” The Paul Bunyan giant statue nods to King and the lumber history of Bangor.

Take historic tours, walk around City Forest, or tap into your inner child at the Maine Discovery Museum. Beyond that, Bangor offers a vibrant arts scene with museums, theaters, and live music venues.

Carrabassett Valley & Sugarloaf

A 2-hour, 15-minute drive perfect for people who just want to get on the slopes and ride all day.

In Maine’s Carrabassett Valley, there’s a ski resort that is as much a location as it is a state of mind. Sugarloaf’s iconic runs just keep growing each year, and it’s the only place in the East with above-the-treeline lifts.

It only makes sense that the Main Ski & Snowboard Museum is among the lodges and cabins. More adventures await at the Sugarloaf Outdoor Center, and Bigelow Preserve is across the highway with more snowy adventures near Flagstaff Lake.

A wonderful waterfall is also tucked away on this winter day trip from Portland Maine. Jericho Steps Falls sits less than 1 mile off Route 27 (Main Street), about 4 miles north of Kingfield. Most of Maine’s magnificent waterfalls are hard to reach in winter, but not this one.

Saddleback & Rangeley

A 2.5-hour drive perfect for immersing your senses in the Maine Lakes & Mountains Region.

Saddleback has been through decades of turmoil as rough as the road to get there — bring a high-clearance vehicle or choose another ski resort. It isn’t fancy and doesn’t want to be anything but raw Maine outdoor adventures.

Explore the lakeside mountain town of Rangeley while you’re here. You’ll get a dose of history and charm while falling in love with the mountain views. Try to stay past dark to see the night skies, some of the most impeccable in the East.

More Winter Day Trips From Portland Maine Await

These are just a few of our favorite Maine day trip options from Portland. For instance, the ferries out of Old Port in Portland run in the winter. While the convenience is for the number of commuters who live offshore, it’s a bonus as a tourist. You can reach several of the Casco Bay islands — Peaks Island, Cliff Island, Chebeague Island, Long Island, Diamond Cove, Great Diamond, and Little Diamond.

Additionally, the Maine Interconnected Trail System has thousands of miles of snowmobiling routes that make for wonderful day trips. The start of the route is 44 miles from Portland in Lebanon.

NOTE: If you’re traveling I-95 between Kittery and Augusta, that’s the Maine Turnpike, which will come with tolls. If you’d rather get a ride to the ski resorts, look for options like Maine Ski Shuttle.

On top of that, reaching the farthest end of the state at the Canadian border is no more than a five-hour drive each way. That makes Maine one of the easiest places to see new places on a day trip. Plan yours today!