42 Hours in Maine: Iconic New England Holiday Getaway
weekend full of holiday events, shopping, and festive fun
Portland + Freeport Winter Itinerary
Looking for the perfect mix of holiday cheer and coastal charm? Plan a magical winter weekend in Portland and Freeport, Maine. Explore our working waterfront and historic streets in Portland, then head to Freeport for classic New England holiday events like the Sparkle Celebration. Whether you’re planning a group holiday shopping trip with friends or a family weekend filled with kid-friendly fun, this itinerary offers the best of Maine’s seasonal experiences. Dive into holiday spirit and enjoy the warmth of the season during your own iconic New England Holiday Getaway.
Day 1 | Portland, Maine
Portland, Maine is easy to access in winter, with direct flights from major cities like New York, Chicago, and Washington, D.C. For drivers, it’s a quick trip up I-95, just under two hours from Boston. Once there, Portland’s compact downtown—less than 4 miles end to end—makes exploring a breeze. You can walk from world-class performances at historic venues like Merrill Auditorium and State Theatre to renowned restaurants in Portland’s Old Port and beyond. Learn more.
mORNING | Holiday cheer + COBBLESTONE CHARM
Kick off your weekend in the heart of downtown Portland, where charming cobblestone streets meet the salty breeze of Casco Bay. Local shops fill windows with festive displays for you to bask in on your walk. Grab a warm drink at one of Portland’s beloved local coffee spots and a sweet treat at a Maine bakery while you feel the winter chill melt away sipping and strolling through the historic Old Port.
The early morning light bouncing off the harbor provides the perfect backdrop for a peaceful start. Learn more.
Afternoon | fine-dining to casual waterfront eats
It’s time to refuel. Stop for lunch at one of Portland’s casual or fine-dining restaurants for an unforgettable meal. Portland is known for its thriving food + drink scene, so whether you’re craving farm-to-table or fresh seafood, there’s a spot for everyone at our table. Not to mention the fact our tables are oceanside with a front row seat to Casco Bay.
Take in the lobster boats and seagulls carving their way across the bay. Learn more.
evening | holiday shows + accomodating hotels
Pair the city’s unforgettable food and beverage with twinkling Pandora Winter lights – an annual light display brightening our downtown all Winter long – and you have the perfect ending to a magical first day. Catch annual holiday shows, events, and performances. Find seasonal experiences likes special cocktails and cozy comforts like a private, heated igloo. End the day in modern luxury or a historic inn.
From boutique hotels to recognizable chains, Portland offers a range of accommodations to suit your style. Learn more.
Day 2 | Freeport, Maine
Just 30 minutes north of Portland is the charming New England waterfront town of Freeport, Maine. Whether you’re wandering quaint streets, enjoying outdoor adventures, or diving into annual holiday events, Freeport feels like a natural extension of any Portland visit. Its close proximity to the city, paired with its own standout attractions, makes Freeport a must-see on any New England holiday getaway itinerary. It’s the best of both worlds: city energy meets coastal retreat. Learn more.
Morning | holiday shopping + seasonal delights
Freeport’s reputation as a shopping destination precedes it, and this is the perfect time to check off some holiday shopping. Explore the iconic L.L.Bean Flagship Store. With festive holiday décor and Northern Lights display, it’s the perfect place to start soaking-up the seasonal atmosphere.
Wander the charming downtown streets filled with a mix of local boutiques and global brands. Learn more.
Afternoon | events + annual celebrations
After lunch, dive into the heart of Freeport’s Sparkle Celebration. Events like the Frosty Frolic offers live music, food trucks, and family-friendly activities that embody the holiday spirit. From horse-drawn carriage rides to visits with Santa, there’s something for everyone. There’s winter and holiday events scattered across the season, so check out the Events Calendar for even more.
evening | nightcaps + holiday festivals
As the sun sets, the holiday magic in Freeport truly shines. If you came during Sparkle Celebration the Parade of Lights illuminates the town with sparkling floats and festive cheer, while the famous Talking Christmas Tree entertains kids and adults alike. Freeport also has seasonal bites + brews at local restaurants, so you can sip and snack in the cozy comforts of fireplaces in quaint New England luxury. Learn more.
how to plan a trip to portland, maine
Ready to start planning your trip to Maine? Here’s where to start. Start by saving this itinerary to your trip plan below. This will help you save all the events and activities you want to participate in while in town. Use our blog and destination site to start filling in the gaps of your upcoming winter getaway. Start here.
