A Weekend Filled with Holiday Events, Shopping, and Festive Fun
Winter Itinerary for Portland + Freeport
Are you searching for the ideal blend of holiday spirit and coastal beauty? Create a memorable winter weekend in Portland and Freeport, Maine. Discover the working waterfront and historic streets in Portland, then continue to Freeport for classic New England holiday festivities like the Sparkle Celebration. Whether you’re organizing a holiday shopping trip with friends or a family weekend filled with activities for the kids, this itinerary showcases Maine’s best seasonal experiences. Embrace the holiday spirit and relish the warmth of the season during your iconic New England Holiday Getaway.
Day 1 | Portland, Maine
Portland offers easy winter access, with direct flights available from major cities like New York, Chicago, and Washington, D.C. For those driving, it’s less than a two-hour journey up I-95 from Boston. Once you arrive, you’ll find that Portland’s compact downtown stretches under 4 miles from end to end, making it incredibly easy to explore. You can stroll from world-class performances at historic venues like Merrill Auditorium and State Theatre to acclaimed dining options in the Old Port and beyond. Learn more.
Morning | Holiday Cheer + Cobblestone Charm
Start your weekend in downtown Portland, where picturesque cobblestone streets meet the refreshing sea breeze of Casco Bay. Local shops showcase festive window displays that invite you to stop and enjoy. Grab a warm beverage from one of Portland’s cozy coffee shops and treat yourself to something sweet from a local bakery, while the winter chill fades away. Take a leisurely stroll through the historic Old Port.
The soft morning light reflecting off the harbor creates a beautiful setting for a serene beginning to your day. Learn more.
Afternoon | Fine Dining or Casual Waterfront Eats
Time to refuel! Enjoy lunch at one of Portland’s casual or upscale restaurants for a delightful meal. The city boasts a vibrant food and beverage scene, offering everything from farm-to-table dining to fresh seafood. Whether you prefer a relaxed atmosphere or a refined culinary experience, you’ll find a spot that suits you, often with a beautiful view of Casco Bay.
As you dine, watch the lobster boats and seagulls navigating the harbor. Learn more.
Evening | Holiday Shows + Comfortable Hotels
Finish your magical first day by enjoying Portland’s delectable dining complemented by the enchanting glow of the Pandora Winter lights—an annual display that brightens downtown throughout the winter. Attend annual holiday performances and events. Experience seasonal delights like specialty cocktails and cozy accommodations, including private, heated igloos. Regardless of your taste, Portland provides modern luxury and historic inns to match your preferences. Learn more.
Day 2 | Freeport, Maine
Just 30 minutes north of Portland lies the charming coastal town of Freeport, Maine. Whether you’re strolling through quaint streets, enjoying outdoor adventures, or participating in annual holiday events, Freeport beautifully complements your Portland visit. With its proximity to the city and its own unique attractions, Freeport is a must-see during any New England holiday getaway. It perfectly combines the vibrant energy of the city with the tranquility of the coast. Learn more.
Morning | Holiday Shopping + Seasonal Delights
Freeport is renowned as a shopping hot spot, making it the perfect place to get a head start on your holiday shopping. Explore boutique stores like Toad&Co in Freeport or Portland for outdoor apparel and grab a steaming cup of coffee. Adorned with festive decorations and a Northern Lights display, downtown Freeport is the ideal setting to soak up the seasonal atmosphere.
Stroll through charming streets filled with a variety of local shops and global brands. Learn more.
Afternoon | Events + Annual Celebrations
Post-lunch, immerse yourself in Freeport’s Sparkle Celebration. Events like the Frosty Frolic feature live music, food trucks, and family-friendly activities that celebrate the holiday spirit. Enjoy horse-drawn carriage rides and visits with Santa, ensuring fun for everyone. With holiday festivities throughout the season, be sure to check the Events Calendar for additional activities.
Evening | Nightcaps + Holiday Festivals
As evening falls, Freeport’s holiday magic truly comes alive. During the Sparkle Celebration, the Parade of Lights brightens the town with dazzling float displays and joyous celebrations, while the iconic Talking Christmas Tree entertains both kids and adults. Enjoy seasonal delights and refreshing beverages at local eateries as you relax by a cozy fireplace, indulging in the charming ambiance of New England luxury. Learn more.
How to Plan Your Trip to Portland, Maine
Ready to start planning your trip to Maine? Here’s how to begin. Save this itinerary to your travel plans below, as it will assist you in keeping track of the events and activities you want to experience while in town. Use our blog and destination website to fill in the details of your upcoming winter getaway. Start here.
