5 Winter Activities in Portland Maine That Will Get You in the Holiday Spirit

Although Portland’s lovely sea breeze and outdoor attractions appeal to the masses during warmer months, you will be surprised to know how many fun activities the city has to offer in winters too. It becomes a winter wonderland, where the beautiful lighthouses blanketed in snow makes you feel like you’ve actually walked inside a snow globe and just about everywhere is decorated for the holidays to help get you in the spirit.

5 Winter Activities in Portland Maine That Will Get You in the Holiday Spirit

1. See the Portland Head Light Surrounded in Snow

There are many lighthouses along Maine’s coastline from Kittery to York’s Nubble Light, but the most famous is Portland Head Light at Fort Williams Park. Completed in 1791, the quintessential lighthouse is the state’s oldest one and has a rich historic significance with spectacular ocean views.

I’ll be honest, the Portland Head Light is stunning during any season, but there is nothing quite as magical as seeing it surrounded in snow. There is also something mesmerizing about watching the waves crash against the snow covered rocks with the lighthouse as the backdrop.  This is what makes it a popular place for the locals to take their holiday pictures!

On a clear winter day you also have the chance to spot four other lighthouses—Spring Point Ledge Light, Cape Elizabeth Light, Ram Island Ledge Light and ten miles beyond that, the Halfway Rock Light Station.

FYI—If you take The Real Portland Tour you will make a stop at the Portland Head Light, along with two other lighthouses. It also takes you on a full city tour guided by a local who was born and raised right in the city!

2. Shop the L.L. Bean Flagship Store 

Maine’s city of Freeport is just outside of Portland and one of the favorite shopping areas of tourists and locals alike. It is filled with charming shops, a cute downtown area, and a handful of national outlets, as well as tasteful locally owned boutiques. But, what it may be known for the most is for being the home of the L.L Bean Flagship Store.

This L.L. Bean location is a 7-acre campus that includes a cafe and a home store. And the best time to go is in the winter when it’s all delightfully decorated for the holidays. Just shopping the complex during the holidays is bucket list worthy, but even if shopping is not on your agenda it’s still worth a visit for the festive decor. There is a pretty forested walk filled with locally sourced evergreens, a warming hut that is the perfect place to drink a mug of hot chocolate with friends and you may even get to visit with Santa Claus. Plus, don’t miss posing with the famous L.L. Bean boot out front and inside their 3,500 gallon fish tank!

It’s purely a bonus that it is open 24-hours a day, 365 days a year and has no locks on its doors! Whether you need a warm flannel, a popup tent or just to get into the Christmas spirit, this store has it all.

3. Tour Victoria Mansion While it’s Decorated

Built around 1860, the ornate Victoria Mansion is impressive with its vintage look and captivating history. Everything about it is stately including the exterior balconies and verandas, and the interior décor of gilded surfaces, original wall paintings, detailed Victorian furniture and a large stained-glass skylight. But, what makes this place all the more fascinating is seeing it decked out for the holidays.

During the winter months Victoria Mansion is transformed into a merry attraction that draws thousands of visitors of all ages. Each year they pick a theme, then artists and designers donate their time to turn the interior into one of the most popular winter activities in Portland. There is definitely something special about seeing each rooms festively decorated trees and wreaths with a backdrop of heavily fringed drapery and highly detailed woodwork.

A visit is not only about seeing the dazzling decor, it is educational too. Each room has a knowledgeable guide who will tell you all about the mansion from its origins as a summer residence for hotelier Ruggles Sylvester Morse to being bought by a resident of Maine who converted it into a museum.

4. Shop & Sip at Merry Madness

Shopping, wine and friends always go together in my book. Who’s with me? If you agree then you definitely need to plan your trip to Portland in December for Merry Madness. During this event, more than 75 stores stay open late so you can shop until you drop. What’s even better is that most offer snacks, sweets and pours of wine!

The fun all starts with the Merry Madness Kickoff Party where you pick up your commemorative stemless wine glass and your first pour of wine! You will also be given a map of participating shops and a reusable shopping bag (you’re gonna need it). Then you’re off to find some holiday treasures. There is no rhyme or reason to which order you shop in, but if you’re anything like me, you’ll follow the wine…

Merry Madness Tips:

  • Most people dress in festive attire, and you should do the same! It doesn’t have to be head-to-toe, but at least a Christmas Light Necklace, a holiday Bow Tie or a festive headband like this one. And if you have a beard please wear these Beardaments (and send me a photo!).
  • You must buy tickets in advance for this event. You can find more information on this website.

5. See the Nutcracker 

There no other winter activity that can get you in the holiday spirit quite like seeing a performance of the Nutcracker. The ballet is a recurrent favorite in Portland and a big part of many people’s holiday tradition. Each season the nationally acclaimed Maine State Ballet presents this show at The Merrill Auditorium.

It is mesmerizing to see the almost 200 dancers gracefully take the stage as they tell the classic and beloved story of Clara and the Nutcracker Prince with ambitious choreography, splendid sets (the Christmas tree is 40 feet tall!) and remarkable costumes. This is all complemented by the orchestra’s live music that is so good it will give you goosebumps. The two-hour show is an activity that the whole family will enjoy.

Where to Stay

Portland has no shortage of lodging options in every price range—from budget to luxurious. Just take a look at the top Hotels on Booking.com. Here are two that I stayed in and recommend.

Inn by the Sea

This oceanfront luxury resort is only a few minutes drive from Portland and a few minutes walk from Crescent Beach. The rooms are warm and tastefully displaying local artwork. My cozy 2-bedroom suite was like having my own little cottage apartment complete with a kitchen and fireplace. But, the best part was the huge bathtub that was a little piece of heaven (it was so big that my feet didn’t even touch the end!).

The restaurant and lounge serve up delicious food, but definitely don’t miss out on the lobster tacos. They used to be a special, but were so good they had to add them to the menu.

A bonus for many pooch owners is that the resort is set up for you to bring your four-legged friend with you. A third of the rooms are dog friendly, you can eat with them in the lounge (there’s actually a gourmet dog menu!) and they offer lots of dog programs. No worries if you don’t have a dog, because you might have one before you leave. The Inn by the Sea fosters dogs and there is usually one on site. It’s not unheard of for one of the guests to adopt this puppy and bring him home.

{Book Here}

121 Middle-an Urban Inn

121 Middle is a budget friendly option for those who want to stay in the midst of all the fun. It’s in the heart of Portland’s downtown, so you can be a part of all the holiday festiveness while being close to your lodging.

The residential style accommodations have simplistic yet classy layouts and décor to keep you comfortable, with all the basic amenities and complimentary Wi-Fi. The technology advanced inn bypasses reception with digital check-in that is an app on your phone.

{Book Here} 

With its winter activity options and holiday events Portland can easily get you in the holiday spirit. From shopping to shows and culture to cuisine it has all the ingredients for a perfect winter getaway.

This post may contain affiliate links. If you make a purchase through my links, I earn a commission that helps to keep this blog running—at no extra cost to you. For more information read my full disclosure.

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