Guide to Portland, Maine in January

My mom, sister, and I took a girls trip to Portland, Maine this winter - during the first week of 2020 - and had such a sweet time together. Portland’s been on my radar for so long, I was so excited to visit and document our stay!

I didn’t know what to expect of a trip to Portland in such a chilly time of year, but after some planning ahead and the packing of proper winter clothing (a big success as Floridians), we were pleasantly surprised by the amount of fun activities and beauty that this part of Maine had to offer us in the wintertime. I can only imagine that visiting in the spring, summer, or fall would be even more magical – but if you’re planning a trip to Portland in January, then this guide is especially for you!

Special thank you to Sally and Emmett for your helpful recommendations!

Things to know before visiting Portland in January:

You’ll need to rent a car! Although Portland is small and would be SO walkable in the spring, summer, or fall, the farthest you may want to walk this time of year could be a handful of blocks before dipping inside.
The weather fluctuates so much! A couple weeks out from our trip, it looked like we’d be getting lots of rain and snow, but by the time we actually arrived, we had more partly sunny days, one rainy day and only a dusting of snow.
It gets dark around 4:15pm - so plan ahead if you want to catch pretty sunsets at lighthouses. ;)
Portland is actually known for getting lots of sunny winter days! With our proper coats and layers, we weren’t too bothered by the chilly weather at all.
Portland has been written up in tons of popular blogs and magazines (Like this article from Bon Appétit naming it the 2018 Restaurant City of the Year) so this has led to more year-round tourism! If you’re planning a visit in the spring, summer, or fall, know that the spots I share in this post are likely to be busier. Of course, the weather would be magical in those seasons - with tons of scenic things to experience outdoors - so it seems like a fair trade off to me.
There are some pretty fun perks to visiting Portland, ME in the winter like…
- Shorter waits/lines at really popular restaurants and bakeries around town! (Hello full selection of flavors at The Holy Donut!)
- Exploring scenic, snowy lighthouses with hardly anyone else around.
- Sledding and skating in a little winter wonderland, baby.
- You’ll likely get free access to a lot of lighthouse parks and state parks!
A downside is that some restaurants close for a winter break or for the winter season (like Portland Lobster Co.) - so be sure to double check on favorites beforehand if that’s important to you. Of course, because Portland’s year-round tourism has grown so much in the last few years like I mentioned, we really didn’t run into this more than 3 times.
When booking your place to stay, I’d recommend finding an area close to Downtown/Old Port! We stayed HERE and LOVED the location.

THINGS TO DO:

Walk around Old Port, and visit all the cute shops throughout Portland! If the weather isn’t snowy or rainy, and you have proper winter clothes/ coats, this would be a really fun way to spend an afternoon.
Spend time reading at a cozy coffee shop (like Tandem Coffee + Bakery).
Eat at tons of incredible restaurants around town!
Visit the Portland Museum of Art (buy your tickets online for less)
Visit Lighthouses! We loved:
- Portland’s Head Lighthouse
- Bug Light
- Spring Point Ledge Lighthouse

Macworth Island - really pretty coastal area to walk around
Check out the East Promonade for a scenic view of the water.
Pick up a sled at a convenient store and go sledding!
Two great sledding spots in town:
- Edward Payson Park
- The Park at Portland’s Head Lighthouse
Boothbay Botanical Gardens - if you arrive closer to January 1, you might make it in time for their holiday light display.
Ice Skating in Falmouth, Maine - They have a really lovely outdoor skating area where you can skate for free! We only paid $2 each to rent skates in the season we visited (subject to change so double check).

FOOD

Rose Foods - a great spot for brunch or lunch. Their bagels are absolutely wonderful and their cafe is so beautiful! Be sure to grab one of their famous totes while you’re there too. (Note that they close at 2pm while we were there in January)
Union Bagel - another great spot to pick up bagels on the go. (There’s no seating here!)
Pai Men Miyake - amazing ramen, delicious buns and cocktails!
CÔNG TỬ BỘT - Vietnamese
Taco Escobar - great lunch spot
Highroller Lobster Co. - open in the winter season for lobster rolls!
Baharat - Middle Eastern restaurant - one of my favorite meals we had!
Duckfat - SO great! Be sure to try the poutine and end your meal with one of their milkshakes!

Places that we Couldn’t Visit This time (But wanted to!!) all recommended by locals:

Honey Paw - seafood + Asian fusion restaurant
Scales (renowned upscale seafood restaurant)
Teralingua
Minato
Fourth Street/ Even Tide
American Bayside Cafe (for great breakfast/brunch)
Hot Suppa (for great breakfast/brunch)

Closed for season

Portland Loster Co.

Popular spots that might be on winter break!

Empire Chinese Food
Central Provisions

COFFEE

Tandem Coffee - they have a roasting location and a location with a bakery - I would highlight recommend visiting their bakery!
Bard Coffee
Higher Grounds Coffee

DRINKS

Four River Brewing Co.
Goodfire Brewery
Hunt and Alpine (cocktails)

BAKED GOODS

Standard Baking Co. - absolutely incredible. Try their almond croissant if you’re there on the weekend - but be sure to go in the morning for the best selection of pastries all around.
The Holy Donut - we went multiple times! The dark chocolate sea salt donut was definitely our unanimous favorite.
Tandem Coffee and Bakery - their biscuits (savory or sweet) blew my mind, and their sticky buns come highly recommended!

SHOPS

Case of You (my personal favorite - I love the beautiful, sustainable brands that they carry)
Find Thrift Store
Pinecone and Chickadee (cute shop next to Find)
Little (near Old Port) - if you have small kids, this shop is a magical place to check out
Flea for All (open on Saturdays and Sundays)
Gus and Ruby - super cute stationary shop
Venn + Maker - home goods
Campfire Pottery - down the street from Venn + Maker
Blanche + Mini