Winter in Portland
The coastal city of Portland, tucked into Casco Bay, bustles with arts, entertainment, and, frankly, too many incredible restaurants to possibly enjoy in one year, let alone one trip. Winter in Portland is a quieter time than summer and the city welcomes those who appreciate the beauty of the season.
Much of the city is on a peninsula, making it easy even in winter to ditch the car and head out on foot. The working harbor, complete with lobster boats, the Old Port with its iconic cobblestone streets, and downtown are minutes apart, and crossing from one side of the peninsula to the other, known as the West End and the East End, is only about a 30-minute walk. Grab a pair of cozy Bean Boots, and head out for all the food and wintery Maine fun you want!
Restaurants
Many visitors come to Portland for the restaurants – and it’s easy to see why. Venerated favorites like Fore Street and Street & Company consistently amaze and the ever-growing list of new and incredible spots like Twelve, Leeward and Chaval bring new flavors and vibes to the historic city and unlike many seaside hotspots, Portland’s restaurants are open year-round.
Maine’s growing brewing, distilling, and fermenting scene is on display in Portland and has outgrown the Old Port, where it all began with Gritty McDuff’s. Head towards Munjoy Hill on the East End and you can find Hardshore Distilling Company, Oxbow Blending & Bottling, Lone Pine Brewing Company, and the Urban Farm Fermentory all within walking distance from each other. The Portland Food Map is a great resource for all things food and drink in Portland, too. If you’re on the hunt for Maine’s best dining, consider going beyond just Portland and enjoy an award-winning restaurant itinerary across the state.
Things to Do
Foodies come to Maine in all seasons and Maine Day Ventures offers culinary walking tours like Portland’s World of Flavors and Savor and Saunter The East End even in the winter. Stroll through town and warm up at the many stops to sample something local and tasty.
No trip to Portland is complete without a visit to the Portland Head Light – perhaps the most recognizable lighthouse in the country. While not technically in Portland, the lighthouse is breathtaking in winter, when snow and ice line the rocky shores, framing the keeper’s house and tower. Sun or snow, you can always walk along the Portland Freedom Trail, a tour that takes you to important sites in African American history, specifically those dealing with 19th-century Black Mainers who stood in the vanguard of the fight against slavery.
Or maybe you want to skate away from it all – you can (if the weather cooperates) at Deering Oaks Park and at the rink at Thompson’s Point with great views of Portland and the Fore River, a state-of-the-art rink, beer garden, and warming areas.
Winter shopping in Portland means unique boutiques, vibrant galleries and delightful shops. Peruse gorgeous textiles and furniture from angela adams or pick up a highly coveted Sea Bag. Find something sparkly at jewelers like D. Cole or Arcana. Find the newest kitchen gadget or one of the many distinctive vinegars and olive oils at LeRoux Kitchen. There are many clothing boutiques and inspiring toy stores, so you are sure to find the perfect gift for everyone on your list.
Portland is definitely for art lovers: museums, galleries, plays, concerts, you name it; Portland’s rich arts and culture offerings are a popular draw in winter. Don’t miss the Portland Museum of Art – always free to the public on Fridays. Most streets are home to one or more galleries as well. Local theaters include Good Theater and Portland Stage and for music, head to the State Theater, the Portland Symphony Orchestra, or Merrill Auditorium – in addition to the many smaller venues that have live shows.
The Children’s Museum and Theatre of Maine is an incredible spot for kids of all ages to create and explore in the winter (and while being inside and warm.)
Accommodations
There’s no shortage of unique places to stay in Portland. Ease into a relaxing weekend at a charming bed & breakfast in a quiet neighborhood, or enjoy proximity to the city’s delights in a modern hotel downtown. Choosing where to stay might be nearly as difficult as where to eat.