Portland is such a great city to explore year-round, and the winter season is no exception! As one of the coolest places in New England during the holidays, winter kicks off with a bang in December, and continues to offer so many ways to enjoy the chilly weather, or cozy up inside, throughout the winter season.
This post is all about the very best things to do in Portland, Maine in the winter, so bundle up and let’s jump in together!
Is Portland, Maine Worth Visiting In The Winter?
Oh, most definitely! In fact, it’s my personal favorite time to visit because the hotel rates are far less expensive than the summer, the city seems much quieter, and the popular attractions are far less crowded. This is a great time of year to explore museums and go on some awesome tours, too.
And since Portland offers a great mix of things to do both indoors and outdoors in the winter, you’ll be able to get a good dose of fresh air, but still have options for really fun things to do in inside to get warm.
On top of that, if you get lucky enough to experience a snowfall, seeing the city covered in a dusting of fresh snow is a magical experience!
Best Things To Do In Portland, Maine In December At Christmas
Portland, Maine is a great destination to find some Christmas cheer and begin your holiday festivities. Because there are so many amazing Christmas celebrations in Portland, I’ve created a separate section on all the best things to do in December.
1. Explore The Holiday Markets
To check a few things off your Christmas shopping lists, the holiday markets in Portland are a great place to start. With a few different options for craft fairs and artisan vendors displaying their handcrafted pieces, these are awesome places to find unique gifts that support small businesses.
Here are some holiday markets to check out in Portland:
- Running With Scissors Open Studios & Holiday Market – Portland artists open their studio doors to shoppers, and offer up treats and special gifts crafted for the holidays!
- Last Call Christmas Arts & Craft Fair – Tons of Maine and New England artisans gather together to sell their pieces, including everything from specialty foods to knitwear.
- Maine Made Holiday Arts & Crafts Show – Very similar to Last Call Christmas, you’ll find local vendors here selling unique items for everyone on your list.
2. Shop ‘Til You Drop During Merry Madness
If you still have some people to shop for after your visits to the holiday markets, you’ll want to mark your calendar for the Merry Madness event in downtown Portland. This is truly a one-of-a-kind shopping event that is guaranteed to get you in the holiday spirit.
During Merry Madness, over 70 Portland retailers offer special discounts, treats and beverages for shoppers, and many shops stay open late (until 10pm!), allowing you to turn the event into a fun night out with friends and family.
Merry Madness kicks off with a party, where participants are welcomed with commemorative glass with a complimentary drink, a reusable shopping bag, snacks to keep your energy up, and finally, a map of the participating shops.
Pro Tip: To make sure you’re ready to find the best deals, download the Scavify app before arriving to the kick-off party. This app will tell you what the discounts are at each participating shop.
3. Snap Photos With The Gorgeous Christmas Trees
Portland begins to look a lot like Christmas right after Thanksgiving with their beautiful trees and light displays around the city.
The biggest and most popular tree to see is the one in Monument Square. The day after Thanksgiving, the annual tree lighting is held to kick off the holiday season in the best possible way.
But you have to be sure to visit the lobster trap tree at the Portland Regency Hotel in Old Port, and swing by to see the tree in Cape Elizabeth, too!
You can also stroll over to the waterfront and visit the lobster trap tree in front of Luke’s Lobster. And while you’re at it, definitely pop in for an awesome lobster roll!
And of course, downtown Portland will be completely aglow with twinkle lights to put you in the Christmas spirit.
4. See Victoria Mansion Decked Out In Its Holiday Best
While Victoria Mansion is an incredible experience year-round for history buffs, and those with an interest in the Victoria era, it’s especially exciting to tour at Christmas. Each year, local vendors and businesses come together and decorate the entire mansion with Victorian-era designs that are beyond impressive.
And the best part? Each year, the decorations change, so you can come back and have an entirely different experience from year to year.
Pro Tip: Victoria Mansion’s Christmas decorations are up starting the Friday after Thanksgiving, through the first week of January, and is open for self-guided tours Tuesdays through Sundays.
5. Experience A Portland-Inspired Nutcracker Performance
If hearing the iconic music of The Nutcracker doesn’t put you in the mood for Christmas, I’m not sure what will! And during the month of December, you can experience a Portland-infused take on this holiday classic, a Victorian Nutcracker by the Portland Ballet.
With backdrops inspired by Victoria Mansion (mentioned above) and characters from Portland’s history, this special take still has the classic story of the Rat King, Sugar Plum Fairy and everything else you’d hope to see.
Performances are held at both the Merrill Auditorium and the Westbrook Performing Arts Center. Click here for more information!
6. Enjoy A Festive Holiday Show By The Portland Symphony Orchestra
If you love live performances, taking in a show by the Portland Symphony Orchestra is another great way to celebrate the holidays.
For over 40 years, the Magic of Christmas show has been infusing the city with holiday spirit, and showcasing classic songs from iconic holiday movies, Christmas crooners like Nat King Cole, and even sprinkles in a piece from The Nutcracker.
Shows are held at the Merrill Auditorium. Click here for more information!
7. Sip On Holiday Cocktails At Blyth & Burrows
Not only is Blyth & Burrows a fun and unique bar to visit year-round, you’ll definitely want to make time for a stop here during the holidays for a special Christmas-inspired cocktail.
On their holiday menu, you’ll find cocktails like Dickens In A Box, Feats Of Strength, and one of their most popular – FRA-GEE-LAY, which features an impeccably-designed nod to a beloved Christmas movie.
But not only are their cocktails great, the atmosphere in this vintage-inspired bar is beautiful, especially with all the Christmas decorations. And the food menu is the perfect compliment to your cocktail (go for the pretzel bites, you won’t regret it).
8. Visit Batson River’s Holiday Camp
Batson River has a few locations around Maine, and their Portland destination is one you don’t want to miss during both the holiday and winter seasons. But their Holiday Camp events and decorations are next level, so be sure to pencil this one into your itinerary.
During the holiday season, Batson River hosts fun events like Christmas Cribbage, Dress Festive and Get Rewarded nights, movie events and so much more.
And on top of all that, you can still indulge in their awesome cocktails, beers, spirits, and delicious foods.
9. Take A Ride On The Polar Express
Every holiday season, the Maine Narrow Gauge Railroad Company & Museum hosts a magical ride to the North Pole on the Polar Express. Once you step inside the vintage passenger cars, you’ll be greeted with beautiful Christmas decorations, hot cocoa and cookies. And, of course, the big guy himself makes a special appearance.
To remember your journey on the Polar Express, children are given a special bell from Santa’s sleigh, too!
Pro Tip: The Polar Express offers different seating options, including standard, First and Presidential. Each tier comes with different perks, so you can fully customize the trip for your family. But all rides include hot cocoa, cookies and the sleigh bell souvenir.
10. Have The Most Instagram-Worthy Dinner At ViA VECCHiA
One of the most beautifully-decorated restaurants in Portland during the holidays is ViA VECCHiA in downtown’s Old Port neighborhood. This Italian-inspired eatery goes all out to celebrate the holidays, and it’ll be hard to not find yourself distracted by the stunning red floral arrangements that cascade around the bar area.
And, since they feature Italian cuisine, the food totally hits the spot on a chilly December night. You’ll want to consider ordering their pizzas, ravioli and mussels. They also have a wonderful holiday-inspired cocktail menu to round out your festive holiday dining experience.
11. Experience The Casco Bay Parade Of Lights
One of the most exciting things to do in Portland, Maine in December is experience the Parade of Lights along the waterfront. Each year on a Saturday in mid-December, lots of boats string twinkle lights around their vessels and cruise down the harbor for all to enjoy. This event is completely free, making it the perfect way to celebrate the holidays with your family.
Pro Tip: You can also enjoy the Parade of Lights from the water! Book a tour with Casco Bay Lines during the Parade for a really cool perspective of the festivities.
Best Things To Do In Portland, Maine In The Winter
Once the holiday festivities come to an end, there’s still plenty of fun to be had during the rest of the winter season! Below is my list of the best and most fun things to do in Portland, Maine in the winter that allow you to embrace the chilly days, or cozy up indoors.
12. Take A Culinary Tour
Is it just me, or is your appetite just bigger in the winter? If your answer to that question is a resounding yes, then you’ll definitely want to check out a culinary tour through Portland in the winter!
Portland is one of the best cities in the U.S. for foodies, and during your visit, a great option is to take an expert-led guided tour to find all the best spots to eat in the historic Old Port district. During the tour, you’ll visit 5-6 restaurants with tastings at each location. This continues to be one of the best-reviewed tours in the city!
Are you a donut person? Well, you’ve come to the right place! The East Coast Portland in Maine is much like Oregon’s Portland in that there are some pretty epic donut places here. And if you’re looking to sample quite a few, you’ll want to book the Old Port Donut Walking Tour.
This guided tour takes you to three of the city’s best donut places, where you’ll be provided with samples to choose your favorite from the day.
13. Find Your Favorite Hot Chocolate
Pretty much anywhere I go in the winter season, I have to check out the hot chocolate scene, and Portland is an awesome place to do that. There are so many places for a cozy cup of hot chocolate around the city, and I definitely suggest checking out a few different ones to find your personal favorite.
A few of the places I like the best for hot chocolate in Portland are:
- Bar of Chocolate
- Gross Confection Bar
- Gorgeous Gelato
- Dean’s Sweets (the sell hot chocolate mixes to take home that are so good!)
14. Go Ice Skating At Thompson’s Point
One of the best places to hit the ice in Maine is at Thompson’s Point in Portland, and this is one of the winter activities in the city you won’t want to miss.
Not only is the outdoor rink tons of fun on a winter day, they have a lot of features that allows you to really make a day of it including a snack bar, a warming hut inside a yurt with a bar, and fire pits. And since the rink is a short drive from downtown Portland, it’s easy to visit.
Note: Thompson’s Point is closed for the 2022-2023 season for renovations, but they plan to reopen for the following winter season with big upgrades!
15. Soak Your Feet And Have Some Tea!
Probably one of the coziest things you can do in Portland in the winter to treat yourself is make an appointment at Soakology. This cute little sanctuary specializes in foot soaks, massage and fair-trade teas.
During your appointment, you can choose from a variety of soaking ingredients for your foot bath, an extensive selection of teas, as well as cookies, shortbreads and other snacks to enjoy from your comfy chair. For the ultimate experience, you’ll want to consider adding on a massage services, or selecting one of their soak/massage combination packages.
16. Ride The Ferry Around Casco Bay
Yep, that’s right! The Casco Bay Line tour company is open in the winter. So if you enjoy the chilly air and are hoping to see some of that coastline Maine is famous for during your visit, one of the best things to do in Portland, Maine in the winter is to hop aboard and set sail!
There are a few different tours to choose from, including sunrise, sunset and mailboat runs. And the prices are very reasonable, considering that your tour will likely last about two hours.
Pro Tip: If you’re looking to take this tour in the winter, but aren’t super jazzed about being outdoors on the water – no worries! There is plenty of indoor space available, too.
17. Indulge In A Spa Day
One of my personal favorite parts of winter is time for self-care, and a massage is such a great way to invest in your well-being. Portland has some pretty amazing massage places to work out the kinks from holiday excitement and stress.
And since most spas feature a eucalyptus steam room and relaxation area for re-centering, you’ll be able to walk back out into the brisk weather feeling completely rejuvenated.
Here are a few places you can check out for a massage in Portland:
- Nine Stones Spa
- Artne Spa
18. Tour The Museums
Portland is home to some pretty great museums, and the winter season is a great time of year to hunker down inside and really soak up everything they have to offer. And since there’s a big variety of museums, including everything from art to local history to children’s museums, there’s truly something to suit everyone’s interests.
Here are some of the best museums in Portland to check out:
- Portland Museum of Art
- Maine Jewish Museum
- Maine Museum of Photographic Arts
- Maine Narrow Gauge Railroad (home of the Polar Express mentioned earlier!)
- Children’s Museum & Theatre of Maine
19. See The Lighthouses
Portland is home to 3 of Maine’s lighthouses, and while this is a popular thing to do in the summer season, I actually love to visit them in the winter, too.
If if your first visit to Portland is in the winter, I highly suggest trying to squeeze in the lighthouses. The 3 you can visit in Portland are:
- Portland Head Light
- Spring Point Ledge Light
- Bug Light
Portland Head Light is Maine’s most famous lighthouse, and is a must. If you get lucky and experience a fresh snowfall during your visit, the lighthouse is especially beautiful!
Spring Point Ledge and Bug Lights are smaller, but still worth visiting (especially because they’re both very close to Portland Head Light).
I have a lot more information on visiting not only these 3 lighthouses, but the best lighthouses in Maine. Click the link below to check that out!
20. Taste The Seasonal Brews
Not only is Portland’s culinary scene pretty awesome, so is the brewery scene. It’s actually one of my favorite places in all of New England to go beer tasting simply because of how many incredible breweries there are to choose them. In fact, Portland has the most breweries per capita in the entire country!
One of the best things to do in Portland, Maine in the winter is to plan a mini brewery hop (just drink responsibly and plan for a designated driver if needed!).
A few of my favorites to check out during your visit are:
- Bissell Brothers
- Goodfire Brewing
- Foundation Brewing Company
- Liquid Riot Bottling Company
- Barreled Souls Brewing
21. Grab Drinks At Apres & Anoche
If you’re not a beer person, fear not! Portland is home to some pretty amazing places for an awesome vibe and great drinks – Apres and Anoche.
Apres is a really fun place to visit, and I suggest stopping by if you can, even if you’re more of a beer person. Not only is the hard cider awesome, the atmosphere here is such a fun vibe, and they also serve up creative cocktails featuring their ciders and hard seltzers.
Anoche claims to serve up the best gin and tonic you’ll ever have, so that’s definitely enough to pique your interest, right? They also have locally-sourced hard ciders from all over New England, and offer some really great food plates, too. This is a great place to grab a drink and a cheese plate.
And the best part? These two places are both less than a half mile from each other, so you can easily visit both!
22. Have A Night At The Ballet
While the Portland Ballet company puts on a beautiful Nutcracker performance, you can catch a show throughout the entire winter season. Their calendar typically includes performances in February and March, and features the perfect mix of classic like Giselle, as well as newer, contemporary works.
23. Donuts, And Pastries, And Whoopie Pies … Oh My!
I feel like a broken record because I’ve mentioned how great the food is in Portland, but guys, the baked goods scene here is pretty epic, too. And since winter is all about indulging and hibernating, this is the perfect excuse to try them all, right?
Between the donuts mentioned earlier (be sure to scroll back up and check out that donut walking tour!), whoopie pies and all the other pastries, you’ll have a hard time escaping the city without sampling at least a few sweets.
Did you know that the whoopie pie originated in New England? Well, Pennsylvania has also tried to lay claim to them, but most people seem to agree that they were invented right here in New England. So some of the best whoopie pies you’ll ever have can be found in Portland!
Here are some of my favorite places to get whoopie pies in Portland:
- Two Fat Cats Bakery
- The Cookie Jar
- Georgous Gelato
If you’re looking for really good pastries, I also highly suggest Scratch Baking Company, which also has really awesome bagels, in addition to classics like brownies, cookies, cinnamon rolls and so much more. Scratch Baking is in South Portland, and convenient if you’re swinging by the lighthouses.
24. Try For A Strike At Bayside Bowl
One of the most fun indoor activities to do in Portland, Maine in the winter is bowling at Bayside Bowl. Stay warm indoors by renting a lane and enjoying cocktails, comfort food (think nachos, poutine, pizzas and burgers) and sometimes even live music.
Have a large group and looking to make a night of it? No problem! Bayside Bowl takes reservations if you’re looking to book 2 or more lanes at a time. So grab a group of friends and bowl away your winter blues.
Romantic Things To Do In Portland, Maine For Valentine’s Day
Portland is such a great destination for a Valentine’s Day getaway, or just a romantic winter weekend away. If you’re celebrating a special occasion and looking for something fun to do as a couple, here are my suggestions for the most romantic things to do in Portland.
25. Go On The Valentine’s Day Walking Tour
The perfect date idea for a couple of history buffs is the Valentine’s Day Walking Tour through the beautiful Old Port district. Not only will you stop at some of the most historic places in the city, you’ll also stroll by art galleries, parks, the waterfront, as well as some of the oldest buildings in the city. And one of the best parts of any tour is getting a local’s insider tips on the best places to explore on your own.
At the end of the tour, you’ll get to enjoy a special Valentine’s Day themed treat to celebrate the month of love.
Bonus Suggestion: See If You Can Spot The Valentine’s Day Bandit!
During the Valentine’s Day Walking Tour, you’re likely to come across plenty of paper hearts taped all over the place by the Valentine’s Day Bandit (sometimes they’re also referred to as the Valentine’s Day Phantom).
This tradition started in the 1970s, and continues today. At some point the day before February 14th, the V-Day Bandit strikes again by hanging these cute little 8×10 hearts all over Old Port. If you spot one, be sure to savor the moment because it’s such a special tradition!
26. Have A Candlelit Dinner At Broken Arrow
On Valentine’s Day, Broken Arrow hosts a beautiful 5-course tasting menu, complete with drink pairings. And the unique part is, you can choose wine, cocktails or mocktails for your pairing (so you’re not limited to just wine!).
Broken Arrow is a really cool restaurant/bar with a huge focus on locally-sourced ingredients, and perfectly balances creative flavors and comforting favorites. The ambience is also perfect for a romantic Valentine’s Day dinner with low lighting and warm, flickering candles.
27. Have A Romantic Dinner With Oysters & Champagne
It’s no secret that oysters and champagne pair perfectly together, and for a special Valentine’s Day splurge, head out to a cozy restaurant to indulge a bit. Especially because fresh seafood in Portland is next level!
A few places that are perfect for a romantic night of champagne and oysters are:
- Helm Oyster Bar & Bistro
- Eventide Oyster Co.
Winter Day Trips From Portland
If you’re planning to be in Portland for more than a few days, you may want to consider a fun little winter day trip! I’ve explored a lot in Maine over the years, and these are my favorite places for day trips from Portland (even in the winter!).
28. Freeport, ME
Freeport is such an easy day trip from Portland because it’s only about 20-30 minutes north of the city. And even in the winter, it provides a fun and relaxing way to spend your afternoon.
If you happen to visit during the Christmas season, you’ll get to experience the Sparkle Celebration, which includes the Northern Lights display at the L.L. Bean flagship campus.
And speaking of L.L. Bean, it’s worth the drive to Freeport just to shop at their flagship store! Snap a photo with the giant Bean Boot, and then get lost in the huge store, which carries pretty much everything they sell online.
Beyond that, the downtown itself is a cute place to do some shopping with a good mix of both franchised and independent shops, and also has some great places to eat.
29. Newburyport, MA
Newburyport is a wonderful winter day trip from Portland, and is just over an hour’s drive, making it pretty easy to experience. This is one of my all-time favorite shopping towns in New England, and it’s impossible for me to even list all my favorite stores because I pretty much love them all. You’ll also find the vast majority of them to be charming, independent boutiques.
Spend your afternoon strolling through the picturesque Market Square and Tannery Marketplace, walking along the waterfront (which is still delightful in the winter!) and cozying up in one of their amazing restaurants.
30. Portsmouth, NH
Another great day trip from Portland is Portsmouth, NH, which is about an hour or less from Portland. Located in New Hampshire, Portsmouth is a city that feels like a quaint New England town, and is also packed with amazing shops, restaurants and historic streets to wander.
During the winter, you’ll want to check out the very lovely outdoor ice skating rink at the Strawbery Banke Museum and then head over to Pickwick’s for unique shopping.
After your skate, head to Market Square for even more amazing shops (check out Portsmouth Soap Co., Jane Gee and Sault), grab some yummy baked goods and coffee at Elephantine Bakery, and then stroll through the beautiful side streets to admire the architecture.
31. Ogunquit & York, ME
Even though Ogunquit is a famous beach town in Maine, it’s still amazing to visit in the winter! If the weather cooperates, a brisk, wintery walk on Ogunquit Beach is sure to cure your winter blues. And one of my favorite things to do in Maine, Marginal Way, is also amazing in the winter (and especially rejuvenating).
York is very close to Ogunquit, and is home to the flagship Stonewall Kitchen store. Warm up by heading indoors to fill up your basket will all kinds of New England goodies for your pantry (their jellies and brownie mixes are my personal favorites!).
Then swing by Cape Neddick to see Nubble Lighthouse. Depending on when you visit, it may be decorated with lights, or have the very lovely heart wreath hung on the red shack for the perfect Valentine’s Day photo.
Where To Stay In Portland, Maine In The Winter
During a winter visit, I suggest staying in the Old Port district. And while I pretty much suggest staying here year-round if it’s in your budget because it’s walkable to most of the attractions, it’s especially convenient in the winter.
In case of snow, it could be challenging to drive into downtown each day during your visit, but you’ll definitely want to weigh the pros and cons against your budget to see if it’s worth it for you. Old Port tends to be the most expensive area of the city to stay in, but in the winter, you can snatch up some great deals, and it tends to be more affordable.
Splurge: The Press Hotel: Great location in Old Port, very stylish rooms, higher-end furnishings, on-site parking and city views from each room. It also has a fireplace in the common spaces for cozy nights with a drink in hand.
Budget: The Francis: During the winter, you can get some really awesome weekend rates for around $150/night at The Francis. Located just under a mile from Old Port, it’s still walkable to a lot of attractions, and the rooms are updated and modern. There’s also an on-site spa!
You may also enjoy:
- Incredible Stops To Make Driving Between Portland, Maine & Acadia National Park
- Best Things To Do In Maine In The Winter
- Magical Things To Do During Christmas In Maine
- Deciding Between Portland, Maine & Portsmouth, NH
- Best New England Winter Getaways
- Awesome Day Trips From Portland, Maine
- The Most Incredible New England Lighthouses To See
- Tips For Visiting Kennebunkport At Christmas
That’s A Wrap On Things To Do In Portland, Maine In The Winter
Now that you’ve been filled in on all the best things to do in Portland, Maine in the winter, you’re ready to have the perfect getaway during the coziest time of the year. Whether you’re excited to see all the sites, go on a food tour, take in a show, or eat all the best desserts (or all of the above!), you’re definitely in for a real treat during your winter visit.