Portland, Maine Winter Travel Guide

While we love our hometown city in every season, there’s a unique magic in Portland, Maine when the air turns crisp and the streets are covered with a blanket of snow. In this post, we’re excited to guide you through the wonders of a winter visit to Portland.

Discover our curated recommendations for cozy places to stay, warm and inviting eateries, and the perfect spots to savor a winter drink. We’ll also unveil the best winter activities to make the most of your time in Portland, whether you’re seeking a boutique hotel, a comforting meal in a charming restaurant, or a winter wonderland adventure outdoors.

We’re eager to share our local insights and ensure your visit is filled with warmth and unforgettable experiences in our beloved city.

Do

• Old Port: Portland’s historic Old Port district is filled with cobblestone streets, local shops, and delicious restaurants. Spend an afternoon wandering the streets, browsing the boutiques, and stopping for a bite to eat.
• Portland Head Light: This historic lighthouse is located in Cape Elizabeth, just a short drive from downtown Portland. Even in the cooler months, it’s a picturesque spot for a stroll.
• Cross Country Skiing and Snowshoeing: One of our personal favorite activities during the winter is cross country skiing at Oxbow Beer Garden. The Portland Gear Hub is onsite at the Oxbow Beer Garden in Oxford, Maine. They offer cross country ski and snowshoe rentals for use on their trails. After you finish on the trails, enjoy pizza and beer at the Oxbow Beer Garden with plenty of outdoor seating by a fire. There is also a hut on the trails with beverages, music, and fires.
• Fat Tire Biking: Located about 30 minutes from Portland, Pineland Farms is one of a few great locations for fat tire biking. You can rent bikes on-site at Pineland Farms. They also offer snowshoe rentals. 
• Sunday River: Located about 1 hour 45 minutes from Portland, Sunday River ski resort offers great trails for skiing and snowboarding in Maine. With eight interconnected mountain peaks and 139 trails and glades, this is a great option for first timers and pros.
• Thompson’s Point Ice Skating: Nestled beneath the popular Depot Pavilion, the Thompson’s Point Rink provides a fun ice skating experience along the picturesque waterfront of Portland. Skate rentals are conveniently available on-site.
• L.L Bean Discovery Programs: Whether you’re a seasoned winter enthusiast or new to the cold-weather scene, L.L.Bean’s expert-led adventures, including fat biking, cross-country skiing, snowshoeing, and ice skating, offer a diverse range of experiences for everyone.
• Batson River Brewing & Distillery: Known for their impressive holiday decor and cocktails (the mistletoe martini is a must!) at all of their locations, Batson River Brewing & Distillery is a must-visit in November and December.
• Soakology: This cozy spa specializes in foot soaks and also offers massages. Sip on tea and enjoy small bits during your appointment at Soakology.

Eat and Drink

Given that this is our hometown, and with so many fantastic dining options to choose from, we had a REALLY hard time narrowing this down, and thought this section was worth its breaking into multiple posts.

• For food and dining recommendations, check out this guide.
• For morning breakfast and brunch recommendations, visit this guide.
• For drink recommendations, check out this guide.

Stay

• Canopy by Hilton: Located on Commercial Street on the edge of Portland’s historic Old Port district. The Canopy hotel has multiple restaurants, including one of the only rooftop bars in Portland, Luna Rooftop Bar. 
• Longfellow Hotel: Located in Portland’s West End. As you step into the beautifully decorated lobby, you’ll find the Twinflower Café in the morning, which transforms into the Five of Clubs bar in the evening. For an even more relaxing experience, visit the on-site Astraea Wellness Spa.
• The Weldon: Located in Portland’s West End, The Weldon offers beautifully designed apartment-style suites with full kitchens, record players, and luxury touches throughout. Guests enjoy access to a modern fitness center, cozy lounge, and easy walkability to the Old Port, arts district, and waterfront.
• The Westin Portland Harborview: A modern hotel located in a historic building with stunning views of the harbor. The Westin features comfortable rooms, an enclosed rooftop bar, and a fitness center.
• Portland Harbor Hotel: Located near the waterfront, this hotel offers the ideal location for exploring all that Portland’s historic Old Port District has to offer.
• Other: There are lots of hotels in Portland. Prices tend to be higher during the summer and early fall, so if these aren’t available to you, we just recommend staying in the Old Port. 

Thank you for visiting our site! We may make commission off affiliate links (at no further cost to you), but we would never recommend a place we don’t genuinely want to recommend.

Tips for Portland, ME

• Leave your heels at home: The city is laid back, but also some of the streets are cobblestones, which makes walking in heels a potentially hazardous activity. That said, if you’re coming for a bachelorette party or girls trip and want to get dressed up, that would not be abnormal. Just proceed with caution.
• Make reservations early: Portland is known for its restaurants, and they book up quickly. We cannot stress enough the importance of booking reservations as early as possible.
• Skip the rental car: Portland is a very walkable city and parking can be a challenge. Uber and Lyft are both available and recommended for exploring. If you are visiting other cities outside of Portland, then you might want a car.

If you have extra time to explore on your trip, be sure to check out our other Maine itineraries and travel guides:

• Kennebunk and Kennebunkport, ME
• Ogunquit and York, ME
• Portland, ME Summer and Fall Travel Guide
• Portland, ME Family Friendly Weekend Guide
• More coming soon!

– Karen and Kasey