Winter WEEKEND ESCAPE TO Greater Portland

Winter WEEKEND ESCAPE TO Greater Portland

Want to get away for the weekend?

Keep reading for ideas on planning your 2-day winter getaway in Greater Portland!

Come to Portland and the Greater Portland, Maine area, where the outdoors are calling, excellent restaurants are waiting, and there’s never a bad season to visit. 

Plane, Train, Automobile, or Bus from Boston

When you’re coming from somewhere like New York City, the transportation options for getting to the Greater Portland area are straightforward. Most choose to start by flying to Boston. From there, you can rent a car, buy a ticket on the Amtrak Downeaster, or relax as you take a bus with Concord Coach Lines. 

Winter at Lighthouse, Photo Credit: Capshore Photography
Winter at Lighthouse, Photo Credit: Capshore Photography

If you don’t want to deal with using public transportation to get to Portland, you can also choose to land directly at the Portland International Jetport. It’s only a ten-minute drive from downtown Portland making it convenient for all your travel needs.

If you love a good road trip, it takes around 5 hours to drive from New York City to Portland, Maine, but that’s assuming you don’t hit any traffic. Expect to spend longer on the road if you plan to drive from NYC to Portland. 

The great thing about this drive is all the fun places you can stop on the way, like Burlington, Providence, and Boston. Some of them may be a little far from your final destination. If you’re already on the road, what’s to stop you from enjoying some exploring?

Day 1

Friday: Check-in to a Charming New England Stay

Greater Portland has charm in spades and there’s nothing like staying at a classic New England accommodation while visiting our winter wonderland. Find everything from Bed and Breakfasts to chain hotels to luxurious boutique experiences can be found downtown (and beyond).

The Chadwick Bed & Breakfast

The Chadwick Bed & Breakfast provides thoughtful touches that invite a sense of pampering and romance.

If you’re an early riser, head over to one of our boutique accommodations, Chadwick Bed & Breakfast . You can enjoy daily coffee and tea on the front porch, watching the sun rise over the city. The charming and luxurious B&B in the heart of Portland will have you feeling and exploring like a local. Come back for the fall and enjoy warm drinks by their outdoor fireplace in a private oasis in the midst of the bustling city.

There’s no shortage or places to stay. You’ll find area Bed + Breakfasts, like Higgins Beach Inn, which is nestled between Crescent Beach, and Cape Elizabeth, and other unique accommodations, like the Mckernan Inn. The Inn is within the Peter A. McKernan Center on Southern Maine Community College’s beautiful waterfront campus.

You’ll find accommodations to match any style of traveler. Wherever you end up laying your ski hat on the first day of your Winter getaway – drop off your luggage and layer-up, it’s time to get out and explore the coast.

Take in the Sights of the Spring Point Ledge Lighthouse

Spring Point Ledge Lighthouse was completed in 1897 to help warn mariners of a dangerous ledge extending into Portland Harbor’s main shipping channel. Before being built, the ledge was the scene of many shipwrecks due to Portland Harbor being so busy.

Spring Point Ledge Light, Photo Credits: Serena Folding
Spring Point Ledge Light, Photo Credits: Serena Folding

Spring Point Ledge Lighthouse is the only caisson-style light station in the country that you can walk to. The lighthouse is rather picturesque and makes an excellent spot for a photo op while you’re on vacation!

It’s also close to Willard Beach, a small pebble and sand beach. At only four acres in size, it’s likely to be pretty quiet this time of year, leaving you plenty of time to catch up on your thoughts or gaze out at the waves. You’ll be at the perfect spot to walk the Spring Point Shoreway, about a mile each way, featuring lovely views of Casco Bay.

Catch a Maine Mariners Game

As it gets dark, turn your attention to Portland for the evening. South Portland is only a few minutes away by car from Portland. Stop into Portland and catch a Maine Mariners game. The Maine Mariners are a professional ECHL ice hockey team based in Portland.  There’s nothing like a hockey game on a Friday night, so grab a craft beer, eat a hot dog, and root for the home team!

Hockey Player. Photo Provided by Maine Mariners
Hockey Player. Photo Provided by Maine Mariners

Stop for a Cocktail at Luna Rooftop Bar

After the game, walk a few short blocks to Luna, a rooftop bar in the heart of the Old Port at the top of the Canopy Portland Waterfront hotel. The Old Port is where all the action is in Portland, and you’ll have the best view in the city from way up high.

You’re bound to be hungry after the game, so order some nibbles, like the Charcuterie Board, with a selection of meats, house-pickled vegetables, mustard, and baguette. Get in that East Coast state of mind with the New England Clam Dip, served with Simply Salted potato chips for that exquisite bite.

Don’t forget about cocktails, like Sweater Weather, with Plantation Rum, Vanilla Almond Milk, Toasted Coconut, House Made Pumpkin Bitters, and Pumpkin Spice. Or try something a little hotter, like the Peppery Whiskey, prepared with Rittenhouse Rye, Chipotle Pepper, Orange Zest, Mole Bitters, and fresh cracked pepper to warm you up from the inside out. 

Fire pits and heaters will do the trick, too, so you won’t have to worry about the weather while you appreciate the view.

Day 2

Saturday: Get in the Car and Go Snowshoeing at Bradbury Mountain State Park

Good morning! Now that you’re well-rested and have enjoyed a tasty Continental breakfast, it’s time to get in the car and do a little driving. Today, you’re going snowshoeing at Bradbury Mountain State Park! Bradbury Mountain State Park is only a 40-minute drive from your room at Spring Point Inn, so you’ll be there in no time. On the way, stop for a coffee to ensure you’re caffeinated and ready for whatever the day has to throw at you.

Did you forget to bring your snowshoeing gear during your winter getaway to Greater Portland? There are plenty of places to stop on the way to rent snowshoes.  Make sure you’re wearing enough layers and good winter boots. Next, you’ll want to pick an appropriate trail, like the Northern Trail. The Northern Trail is the longest trail that goes up Bradbury Mountain, with a gradual incline of 407 feet over one mile. 

It’s not too challenging and allows you to get outside while enjoying the view. It’s gorgeous and looks as pretty as a picture! You’ll be able to see the surrounding fields and rolling hills of Pownal once you reach the top.

Grab lunch and enjoy a Lobster Roll and a Bowl of Clam Chowder at Linda Bean’s

Lobster. Photo Provided by Linda Bean's Perfect Maine
Lobster. Photo Provided by Linda Bean’s Perfect Maine

After an afternoon of snowshoeing, you’ve probably worked up an appetite! Get the best (no matter the season) by stopping into Linda Bean’s in Freeport. We recommend a cup of creamy clam chowder, followed by a lobster roll. 

If you’re still hungry, the fried whole belly clams are a must. Not a lobster roll fan? You can still get your lobster fix with a lobster BLT or a bowl of decadent lobster mac n cheese you’ll be talking about until you make it home. Plenty of things to do, see, and experience when you Visit Freeport, Maine.

Enjoy the arts with the Maine State Ballet

Dancers Performing. Photo Provided by Maine State Ballet
Dancers Performing. Photo Provided by Maine State Ballet

The Maine State Ballet offers stunning shows of strength, grace, and beauty with every step. Stop in to see their annual showing of The Nutcracker in the winter or in the warmer months, you can view their other shows like Cinderella, A Midsummer Night’s Dream, and more.

Ready to plan your 2-day winter getaway to Greater Portland? Reach out to Visit Portland to learn more!