How to Spend a Summer Weekend in Portland, ME
A city by the sea, defined by its working waterfront and a proud but fading industrial history. A rocky peninsula packed with arts and culture, world-class cuisine, and a few kitchy gift shops for the cruise ship crowd.
Portland is a small town; the downtown peninsula is only about two miles long and one mile wide. A large part of the city’s charm is found from walking around and listening to seagulls gossip overhead, wandering past an art vendor, or overhearing a meeting of two friends on the sidewalk. There is still some port city grit remaining in the corners, but generally the city is ripe for aimless exploration.
It also happens to be our home, and we’d love to share a few of our favorite recommendations with you. The seasons here are defined not only by changing weather but changing crowds, length of days, and pace of life. So, we’re starting with a the season for which Vacationland is best known: summer. The ways to pass the days are as endless as the hours of sunlight in this corner of the world.
WHERE TO STAY: DOWNTOWN
Located just off the city’s famous working waterfront in the heart of the Old Port, the Weldon offers luxury apartment-style suites so that you can feel at home during your stay. We love the curated record selection in each room to help set the mood.
Want to be a little further from the bustle of the Old Port? We love the Victorian-era neighborhood of the West End, where the houses are dressed like ladies in lace doilies and pastels, contrasting the red brick sidewalks they stand on. While the bustle of downtown is just a few minutes walk away, the streets here are quiet. You can really feel at home.
LONGFELLOW HOTEL | Wellness-focused luxury
THE FRANCIS | Boutique BnB full of historical charm (and a delightful tavern attached)
BLIND TIGER | Curated guest house with unique design details in every room.
WHERE TO STAY: OFF THE BEATEN PATH
If you’re willing to leave the penninsula and interested in a little bit more of a respite from the city, there are incredible options just a bit further afield, from luxury beachside accommodations to something...a little bit more adventurous.
INN BY THE SEA | Oceanfront resort with excellent hospitality and two miles of beach access
FORTLAND | Glamping on an island with a historic fort in Casco Bay, accessed by ferry from downtown Portland
WHERE TO EAT
If you don’t already know, Portland is a pretty special place for the culinarily inclined. There are enough independently owned restaurants in town that you could go to one every day of the year and still not make it through the list. This makes is hard to narrow down the best recommendations, but here we have a mix of our go-tos and special occasion favorites.
THE MOST IMPORTANT MEAL
Portland is a city of bakeries. The romance of early mornings stoking hearth fires and hours spent slow-proofing dough fits well with the seaside charm of our little city. Stop for sourdough from a Parisian-style micro boulangerie or the best chocolate chip cookie you’ll ever have, or grab a handmade croissant from almost any coffee shop in town. There’s no shortage of delicious carbs to consume to start your day, or coffee shops to stop at!
BARD | Easy stop in the center of Old Port with pastries from mobile bakery Not A Bakery
MOONDAY | Tiny counter in a refurbished shipping container with the best coffee (and chai) in town, and dlightful baked goods by Mari, a mini bakery
NIGHT MOVES | Just across the bridge in South Portland, this seaside bakery has the best/weirdest brownie we’ve ever tried and mills all of their own flour from native Northeast grains
RADIAL | This is basically the Secret Supper office! Incredible baristas and a view of the water make it the perfect place to grab a quick pastry (They carry Bread & Friends and BLVL, both local favorites) or stay all morning.
TANDEM BAKERY | Biscuits, breakfast sandwiches, and cookies (stick to their roastery location, known as “little tandem” for coffee, though)
ZU BAKER | Perfect croissants (that sell out fast!) and sourdough bread made exclusively with Maine-grown wheat
NOT SEAFOOD
ANOCHE | Spanish-style vermouth bar with tapas on Washington street, a stretch of wonderful shops and restaurants worth wandering for an afternoon
CÔNG TU BÔT | Once you’ve sipped through all the vermouth, head just up the block for Vietnamese noodles.
CRISPY GAI | Thai fried chicken and tropical cocktails (need we say more?)
FRIENDS & FAMILY | Pizza, wine, and good vibes under a gorgeous tin ceiling
LEEWARD | Perfect pasta and a delicate style of hospitality that will make you fall in love
WAYSIDE | Sit at the bar on a rainy night for cozy tavern vibes and exceptional cuisine
WHAT TO SEE + DO
Eventually, you need something to kill time between meals.
BROWSE OUR FAVORITE SHOPS
POST SUPPLY | A curated collection of pretty, practical things
PRINT | Community-oriented independent bookstore
RABELAIS | A one-of-a-kind culinary book shop manned by a human encyclopedia
SKORDO | Locally blended spices for the adventurous home cook
SISSLE & DAUGHTERS | Cheese, specialty groceries, and culinary treasures
Portland has one of New England’s most vibrant organic farming communities. Farmers from across the state bring gorgeous produce, pasta, eggs, meat, cheese, and other treasures to Deering Oaks Park every Wednesday and Saturday in the summer. Whether you’re looking for the best ingredients to cook dinner at your vacation rental or simply want to collect provisions for a picnic on the Eastern Prom, you can find everything you need here. Bonus: There are always really good dogs shopping too!
Wander through the Portland Museum of Art to view some stunning art and architecture, including many works and rotating exhibitions featuring Maine artists. We particularly love visiting in the spring for Art in Bloom, when local florists create beautiful installations inspired by art pieces throughout the galleries.
TAKE A RIDE ON THE FERRY BOAT
After grabbing your morning coffee at Moonday, stop by Sissle & Daughters and ask them to help put together a portable cheese board and snacks for you (don’t forget a good bottle of wine and a wine key), then head to the ferry terminal to jump on the Mailboat, which runs at 10am, 12pm, and 3pm every day of the year. The ferry takes about 2.5 hrs and takes you on a scenic loop of all the Casco Bay islands while the ferry crew...literally delivers the mail.
GET CAUGHT AT THE CROWN JEWEL
If a three-hour tour sounds like more time on the water than you are interested in, hop on the 30-ish minute ferry to Great Diamond Island (there are two stops; make sure you get off at the second one: Diamond Cove). Visit Crown Jewel, a sweet little island escape perfect for brunch or happy hour cocktails. They’ll even pour you wine or cocktails to-go for the ferry back to the mainland.
If you really want a locals experience, be sure to pack a swimsuit and jump off the dock in Diamond Cove before the ferry comes to pick you up!
HEAD TO HANKS
Start the morning with a stop at Higgins Beach Market for beach provisions, then stake out a spot and stay on the beach for as long as you’d like.
On the way home, head to Hank’s. Hank and his mom are there every day, running the shop and making simple food from local ingredients with a lot of care. If it’s still morning, don’t miss the breakfast burrito with house-ground sausage.
But, if it’s afternoon and you’re a little sun-drunk from sitting on the beach, order tater tots and a bottle of rose to share in the backyard. Bring the dog or the kids, if you have them. It’s a perfect way while away the long hours of summer sunshine.
