There’s something about Portland in the winter. The sidewalks are quieter. Reservations are easier to come by. The pace softens just enough to notice the details. It’s the season we locals savor most, and we’d love for you to join us.
To help you experience Portland the way we do, we’ve created this winter weekend itinerary. Consider it your invitation to settle in, explore a little deeper, and enjoy this corner of Maine at its most relaxed. Here’s how we’d spend a winter weekend with you:
Friday Evening: Arrive & Settle In
Check in, drop your bags, and head downstairs to Five of Clubs. A cocktail by the bar sets the tone, unhurried, warmly lit, just lively enough to feel like the start of something.
When you’re ready for dinner, wander across the street to Wayside Tavern for a meal that feels both classic and current. Winter is the time to linger over something hearty and well made, to order dessert even if you hadn’t planned to (we recommend the chocolate mousse).
If the night’s still young, follow your mood. Portland’s creative pulse doesn’t slow with the temperature. Catch live music at One Longfellow Square or The State Theater, settle in for a comedy show, or join the hometown crowd for a hockey game at the Cross Insurance Arena. Then make your way back to The Longfellow for the kind of sleep that only comes with crisp air and a full day behind you.
Saturday: Slow Morning, City Wanderings
Ease into the day with breakfast. If you’re craving something sweet and a little indulgent, Tandem Coffee and Bakery next door is one of the city’s most beloved bakeries. And if you’re in the mood for a classic sit-down breakfast, Hot Suppa is a local favorite (and this time of year you’re much more likely to get a table).
From there, choose your own winter adventure. If you’re feeling outdoorsy, head to Thompson’s Point for ice skating and hot chocolate with a waterfront backdrop. Or make your way to one of Maine’s historic lighthouses, and appreciate these iconic landmarks against a snowy backdrop. Prefer something cultural? Spend the morning at the Portland Museum of Art. Don’t miss the McLellan House, tucked just beyond the gift shop, a quieter corner of the museum and home to some of our favorite works.
In the afternoon, take your time exploring Portland’s independent shops. Our top picks? Viand Mercantile, Blanche & Mimi, Soleil, Fitz & Bennett, The Post Supply, and Baske Home are all thoughtful stops for home goods and small treasures. They’re the kind of places where winter browsing feels personal, unhurried, and a little bit serendipitous.
As evening approaches, settle in for dinner at one of Portland’s celebrated tables. Perhaps Eventide Oyster Co., Fore Street, or Via Vecchia if you’re in the mood for something polished and memorable. Or keep it more relaxed with dinner at Crispy Gai, Highroller Lobster Co., or Minato. In winter, even Portland’s most popular spots feel just a bit more accessible; another quiet luxury of the season.
Sunday: Restore Before the Road
Start your final morning gently. For something nourishing and close at hand, Twinflower Cafe offers wholesome, satisfying bites just steps from your room.
Then ease into the day with a visit to Astraea, our wellness spa just downstairs. Book a private infrared sauna suite to warm through before you travel, or opt for a restorative massage or calming facial. It’s a seamless way to transition from weekend to weekday—and to leave Portland feeling relaxed, restored, and ready for what’s next.
If you’re heading south, consider taking Route 1 and making a few antique stops along the way. Antiques USA and Americana Workshop are worth the slight detour. If you’re heading north, don’t miss Cabot Mill Antiques, and the connected Waterfront Flea Market (only open on Saturdays and Sundays!).
Portland in winter isn’t about doing everything. It’s about doing a few things well. A good meal. A long conversation. A snowy walk. A warm room to return to.
We’ll be here when you arrive.