Your weekend itinerary for a winter stay in Portland, Maine

Updated: January 20, 2023

The state of Maine has been officially known as “Vacationland” since at least 1936. At any rate, that’s when the state’s license plates have borne this well known moniker.

For many, the idea of Maine conjures up images of camping, sandy beaches and lobster bakes. And while you can do all of these things year-round (take it from an avid winter camper) as a destination, Maine is known for its summer delights.

But if you think our state is only for warm weather journeys, you’re missing out. Portland is an idyllic destination for winter vacations, packed with things to do and quaint winter rentals.

That’s why this intrepid former reporter and state traveller is offering his two-day itinerary for your holiday vacation in the Portland area. Whether you’re a snow-bird missing home and looking to make a quick trip, a visitor from away coming to enjoy Maine’s frostiest season, or traveling Down East for a work trip, this schedule is for you. And all the items on the list are no more than 10 minutes from downtown Portland.**

Day 1:

Catch breakfast (or brunch) at Hot Suppa. This West End favorite will give you the sustenance you need for an active first day. If you’re in a hurry–or if you’re in the East End–head to Cumberland Ave. and Coffee ME Up for Albanian baked goods and fresh coffee.

Next, you’re going on a sight-seeing tour of southern Maine’s natural beauty. I hope you brought your cross country skis or snowshoes, but if you didn’t, a decent pair of boots will work fine. Check out these maps from Portland Trails, a great local organization that maintains a series of routes through the wilderness in and outside of metropolitan Portland. Choose whichever route suits you best, but make sure you end your journey near Thompson’s Point (near the Portland Transportation Center).

You’ll want to arrive around sunset, and bring your appetite. At Thompson’s Point, you’ll find Portland’s outdoor ice skating rink. A low admission fee and cheap skate rentals make this a definite attraction. But the warming hut, with a well-stoked fire and Allagash beer on tap, make it indispensable to any Portland winter journey. After you’ve had your fill of skating, grab a bite at one of the food trucks on site, then head across the parking lot to Bissell Brothers Brewing or Cellardoor Winery. Bissell Brothers is one Portland’s most popular breweries, especially for tourists.

If you’re looking for a bit more entertainment, stop by downtown’s Nickelodeon Cinemas on your way back to your vacation rental.

Day 2:

Now that you’ve got your recreation out of the way, time for a day on the town. Start your morning on Commercial Street. This picturesque waterfront boulevard will offer everything you need in the way of eating and shopping. But don’t stay too long. After you’ve had your fill, head towards Monument Square and Congress Street. There you’ll find Reny’s, the closest thing Maine has to an official department store. What are you picking up? Well your souvenirs, of course. Oh, and also a sled.

You’ll be taking that sled to Munjoy Hill’s Eastern Prom. This beautiful park overlooks Casco Bay with views–on a clear day–all the way up to Harpswell Neck. But naturally, you’re here for the sledding. Put that new ride to the test. If you’re curious about the best sledding spots, just follow the kids. On a winter’s day in Portland, there are usually plenty of them riding down the best slopes in the park.

After all that sledding, you might be hungry. Head back downtown via Congress Street. You’ll pass the iconic Portland Observatory on the way. As you get to the bottom of the hill, you’ll find OTTO Pizza, arguably Portland’s favorite pizza place. (Okay, locals, I know that’s a controversial statement!)

Grab a slice, a pie, or a delicious salad and, if the mood suits, a pint of local beer. But don’t fill up! Your next stop is downtown. Continue your walk back toward Portland’s Old Port to Rosie’s, an iconic Portland pub built for winter afternoons. Try the steamed mussels or a bowl of chowder and make sure you chase it with a Guiness or a hot toddy.

For those interested in nightlife, your next stop is in the Portland neighborhood of Bayside. Get your dancing shoes and head to Portland’s longest running nightclub, Bubba’s Sulky Lounge. If you’re there on a Friday, you’ll be treated to a mix of 80s and 90s music. If you’re hitting the town on Saturday, get ready for contemporary pop. This eclectic, colorful, and free-spirited discotheque (yes, I use that word intentionally) invites people of all ages and walks of life. The drinks are cheap (and strong), the floor is pantone, and the crowd is welcoming–not to mention the cover is only $5. Stay till the DJ stops the music, then follow the crowd back to OTTO or, if you’re in the mood for a walk, back down to the Old Port, where you can something to eat from several establishments open late.

When you lay your head down at your winter rental, you should feel proud that you’ve packed so much into your short Portland visit!

Now, I’ve limited my suggestions to a two-day journey in Maine. But I would be a terrible host if I didn’t at least mention some of the near-to-Portland offerings. If you’ve got wheels and you’d like to do some shopping or fine dining, make sure you head up the coast to Freeport (home of L.L. Bean) or to Brunswick. Both cities offer great restaurants and shops. If you’re looking for something more recreational, head north to Bethel, Maine. This small, rural village is near to Sunday River ski resort, but is also a destination in its own right, with several restaurants to warm your belly, miles of cross country skiing trails, and the Bethel Inn (boasting a heated, outdoor pool).

** For those visiting Maine for a skiing holiday, Portland is still a great place to lay your head. But since the three largest ski mountains are all about 2 hours away from the city, I won’t include those on this list. Maybe we’ll release an itinerary just for you skiers and riders soon!

If you’re still looking for you fully furnished Portland accommodations–your home away from home during your seasonal visit to Maine, check out our listings page.