a Winter Weekend in Portland, Maine
6 Reasons to Spend a Winter Weekend in Portland, Maine
It’s no secret how much I adore Maine. A quick scroll through my “Wander” page is all it takes to confirm that point. But you may also notice that my Maine content is void of anything in the winter months. Until now…
Believe it or not, up until last month, I had never visited Portland, or Maine for that matter, in the wintertime. I have been in the spring, summer and fall, all of which are beautiful and wonderful times to visit. But you know when else I discovered is a great time to visit? Winter! It’s so stunning with the snow and there are significantly less tourists, meaning it’s easier to do just about everything {get a reservation, book a hotel room, etc.}. Plus, there are lots of fun activities, from snowshoeing to shopping.
Whether you’ve visited Portland before or not, a winter weekend in the city is definitely something that should be on your radar. Below, I’m diving into 6 reasons why. And yes, lobster is involved {I mean, tbh, did you really think it wouldn’t be?}.
why you should spend a winter weekend here
Weekends Are Easy to Book
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While summer and fall weekends at local hotels typically book out months in advance, fewer tourists means it’s a whole lot easier for you to book a winter weekend away.
This trip I split my time between two properties, both of which were great this time of year, but, depending on your itinerary and the kind of trip you’re looking for, you might prefer one over the other.
INN BY THE SEA
This beautiful and serene property, located right on the water, is only a few miles from downtown Portland, but its peaceful and relaxing environment will having you feeling worlds away. The rooms are beautiful and spacious, the amenities are amazing, there’s beach access directly from the property, the on-site restaurant is serving up delicious food, there’s an incredible spa and I absolutely love the initiatives that the hotel is taking to be more eco-friendly {for example, they provide little bags for you to take home your remaining soap bar that would otherwise go to waste}. And did I mention that they are dog-friendly? Yes, you can bring your furry friend with you AND, even more amazing, they actually foster dogs from a local shelter to help them get adopted! I mean, can I just move in??!
If you are looking for a relaxing winter getaway, if you’re hoping to bring your dog on your vacation with you, this isn’t your first time to Portland and you’d like to experience a different side of the area, and/or you’ll be driving to Maine or renting a car during your stay, I highly recommend staying here.
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Right in the middle of all the action you will find one of Portland’s newest lodging properties. Each unit is essentially a one or two bedroom apartment, and I’m telling you, they’re so beautiful you’ll probably just want to go ahead and move in permanently!
If you prefer more of a home away from home setting, if you’re planning a longer stay, if you like to be in the middle of the action and will be going out a lot {especially late night}, if you want to be able to walk to everything, or this is your first trip to Portland, I would definitely check into booking a stay here.
There are Activities for all
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From shopping to relaxing at the spa to historical tours to outdoor activities to shows, there is literally something for everyone and more than enough to keep you busy through a long weekend. Here are a few suggestions for things to do-
RELAX AT THE SPA // I get it, it’s a bit chilly outside, so maybe you want to spend some time warming up inside, or maybe you need to de-stress from all the holiday madness. And where better to do that than the spa?! Inn by the Sea has a great on-site facility, and I got one of the best full-body massages of my life there. Highly recommend it!
TAKE A TOUR // Portland is packed with fascinating history, so if you’ve never visited the city before I’d suggest taking a tour or two to get acquainted with the background of the area. A few to check out include the Bi-Centennial Tour offered by Maine Foodie Tours, which is a walking history tour around the downtown area, and a South Portland Tour {a great way to see some of the local lighthouses} with The Real Portland Tour.
SHOP // There are no shortage of shops around the downtown area. A few of my favorites include: Skordo {amazing selection of spices from around the world as well as lots of chic kitchenwares}, Seabags {home to the bags made from old sails…the company is based right here in Portland}, Portland Flea for All {for the best vintage finds}, Judith {for a beautifully curated space that you’ll want to live in} and Zane {so many great items and brands featured here}. And, if you happen to be visiting in early December, be sure not to miss out on Merry Madness. It’s festive and fun, there are tons of people out and about, places are open late and serving all kinds of yummy snacks and wine, some of them even have special deals/discounts and it’s really just a great way to check out the local shops in the downtown area.
CATCH A SHOW // There are so many options to choose from, between concerts, the ballet {Hello Nutcracker, if you’re in town during the holidays!} and more. Check out Maine State Ballet, Merrill Auditorium and Portland Stage for a complete list of current performances and to purchase tickets.
OUTDOOR ACTIVITIES // Wintertime in Maine is the perfect time for some cross-country skiing or snowshoeing and, of course, there are tons of great downhill skiing/snowboarding locations not far from Portland. You can find out more here.
It’s Just Not That Cold
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Ok, it’s obviously cold. It IS winter in Maine, after all. You’d be silly to think it wouldn’t be cold. But the one question I kept getting over and over again was how cold it actually was while I was there and if it really is worth visiting in the wintertime. Well, I have news for you. If you’re from New England, or you’ve spent anytime living in Boston or NYC, I promise you the weather won’t even make you flinch. It’s literally the same winter weather you’d find in NY. And if you’ve spent anytime in Chicago in the winter, you’ll practically think it’s summer weather in Portland. Of course, coming from LA, it’s a bit more of an adjustment, but pack the right coat and you’ll have no issues at all.
Here are a few of the things I brought with me to stay warm: a winter hat, scarves, gloves, my packable {and easy to layer under} Uniqlo puffer jacket, basic turtlenecks, a few thick sweaters, thermal underwear {I layered the top under my sweaters}, extra thick tights {to layer under my pants and socks}, wool socks and lined boots.
it’s less crowded
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Translation: it’s easier to do just about anything and everything. You won’t have quite as much trouble booking a hotel or snagging a reservation for an uber popular restaurant, and it will definitely be easier to maneuver around the shops or get a spot on a tour.
One place in particular where I really noticed a difference was the Portland Lighthouse, which we stopped at on The Real Portland Tour. Typically, the area is teeming with people and the parking lot is packed with cars, but during this visit there was almost no one around, and I have to say, seeing the lighthouse dressed in its Christmas best, with snow on the ground, in near solitude, was just such a special moment. That alone is worth a winter trip to Portland!
The Lobster is Just as Tasty
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And so is everything else! I mean, let’s be real, Portland’s food scene is one of the best in the country! It’s also home to some of my all time favorite foods and restaurants. On this trip, however, outside of a few stops I made on my own, every restaurant we ate at was new to me, which made them all the more fun to check out.
Here’s where we went-
SEA GLASS // Located at Inn by the Sea, you can’t go wrong with any of the meals here. Seriously, everything I had, even the tuna melt, was just so well done. Oh, and whatever you do, don’t miss out on the lobster toast for breakfast. It’s beyond divine!
$3 DEWEY’S // An old-school spot, great for grabbing a casual drink and/or some late night bites/bar food {And while this might sound random, whatever you do, you must order the brussel sprouts! They are seriously delicious and some of the best I’ve ever had! Just trust me on this one!}.
THE PORTHOLE // A classic Portland spot right on the waterfront; seafood is the way to go here…you really can’t go wrong with lobster anything and the chowder is also great!
NOBLE KITCHEN + BAR // While this spot is not located in Portland, if you happen to be in the Brunswick area {say, after visiting the Gardens Aglow}, definitely stop here! It’s a cozy spot, there was live music while we were there and the braised short ribs were so yummy! Also, don’t sleep on their desserts…they were all divine {especially the cheesecake and zeppoles}!
UNION RESTAURANT // Went here for brunch and just loved the diverse menu packed with unique options; would definitely recommend checking it out!
QUIERO CAFE // This spot is definitely not what you think of when you think of Maine, which is why I loved it even more. And even better, the food was incredibly delicious! It’s all Latin American cuisine so think things like empanadas, patacon and rice plates. There sauces are delicious {pretty sure I doused my food in at least half a bottle} and I also loved the passionfruit lemonade!
TOP OF THE EAST // The only rooftop bar in Portland; great for sunset cocktails
SUR-LIE // Great to come with a group as they serve tapas-style dishes; lots of fresh, local flavors are used and the resulting dishes are quite tasty; some of my favorite things included their sweet pea hummus, white bean dip and the cod
EIGHTEN95 // We ate our last brunch of the trip here; I got the classic pancakes with Maine blueberries, which were delicious, but huge {you could definitely split them with someone}. Don’t forget a side of sausage or bacon!
I also stopped into a few of my go-to favorites- Tandem {love their coffee and baked goods}, The Honey Paw {the lobster toast is heaven on a plate} and Speckled Ax {great for coffee}.
It ‘s a winter wonderland
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If you thought Maine was pretty in the summertime, or stunning dressed in fall foliage, then you’ll be in for a real treat because it is beyond beautiful when it is blanketed in snow. Add in Christmas decorations {if you visit during the holidays} and it’s truly magical!
A few of my favorite winter wonderland sightings included the Portland Head Lighthouse {Gorgeous with the snow and loved the addition of the wreath on the lighthouse!}, the Christmas “tree” built out of lobster traps {I mean, does it really get more Maine than that?!}, the decorations at the L.L. Bean Flagship store {They even have reindeer!}, the Victoria Mansion {which is pretty all the time, but especially in the winter because it gets all decked for the holidays} and the enchanting Gardens Aglow at Coastal Maine Botanical Gardens {Definitely a bit of a drive from Portland, but if you have a car during your visit, I highly recommend checking it out…seeing the gardens decked out in thousands of lights is so worth the trek!}.
