Most people show up in Portland, Maine, with one agenda: eat as much as humanly possible. Fair enough. This is a city that has a do-not-miss dining list a mile long, featuring everything from lobster rolls to potato donuts. Here’s how to maximize your time and stomach space, along with cultural activities and active pursuits for those rare windows when you’re not drinking or eating.
Friday
Check into The Docent’s Collection and make yourself at home in these loft-style accommodations. The Docent’s Dossier package comes with a build-your-own lobster roll kit from Luke’s Lobster, including fresh meat, rolls, mayo, lemon, and spices, so you can eat your first Maine lobster roll from the comfort of your couch, rather than in line under the hot sun.
Once you’ve recovered, get a coffee at Bard Coffee, where the nitro cold brew will help you shake off any travel fatigue.
Spend a few hours at the Portland Museum of Art (tickets included in the Dossier deal), which spans four floors and features icons such as Winslow Homer and Monet, along with a solid rotation of local artists who deserve the wall space just as much.
After, discuss your favorite artworks over a refreshing shaved ice from Zephyr Ice, where you have to get the blueberry syrup topping.
Enjoy dinner at Ladyfish, a small-plates seafood spot with a lively outdoor patio. Experience true Maine culture by ordering the Moxie float for dessert. Made with the state’s famously polarizing soda, boba, and a scoop of gelato from Fiasco Gelato next door, it’s unique and refreshing. If you want to go full Mainer, add in the Allen’s Coffee Brandy Affogato, which features another New England delicacy, a coffee-flavored liquor, drizzled over ice cream.
Saturday
Start with breakfast at LB Kitchen, where you can get a smoothie enhanced with CBD or electrolytes if you’re still recovering from last night, or a decadent breakfast sandwich if you woke up hungry.
Rent bikes from The Encyclepedia, and pedal out to the Eastern Trail. This mostly off-street ride goes for miles along a paved, relatively flat path, and will show you a side of the city most tourists miss. Cycle to the path’s end at Bug Light in South Portland to see the lighthouse and stunning views of the city.
Return your rides and head to Barkada for a fast-casual Filipino feast for lunch. Spend the afternoon wandering Congress Street, Portland’s main artery, and the waterfront, popping into as many charming boutique shops as you can. When you’re ready for a pick-me-up, stop at Mount Desert Ice Cream and get a split scoop with Blueberry Sour Cream Crumble and Lemon Poppy Jam.
For dinner, book the Chef’s Counter at EVO so you can watch the action up close. This mezze-style restaurant has a menu that will tempt you to order everything, but don’t miss the raspberry beret cocktail and the tomato watermelon salad.
Sunday
Indulge in Sunday brunch at Bread & Friends, where the pastries are the star (specifically, the homemade cinnamon sugar pop tart and the savory everything pull-apart bun).
Work it off with a walk around the Back Cove Trail, a scenic 3.5-mile loop around the water that offers beautiful Portland skyline views.
You can’t leave town without stopping by at the Portland institution, Holy Donuts, donuts made with riced potatoes. Whether they’re actually better for you than a regular donut is debatable, but the taste is undeniable. Ideally eaten fresh out of the fryer, they’re also good to take home and freeze for later as an edible souvenir.
Where to Stay: The Docent’s Collection
If you want all the comforts of home (albeit perhaps a more luxurious home than your own) while you’re in Portland, book a loft at The Docent’s Collection. The property spans three historic brick buildings in the heart of Old Port, right at Old Port Square, a block from the waterfront and even closer to Congress Street, putting you within walking distance of all the best restaurants and shops.
Instead of standard hotel rooms, it offers apartment-style living, with lofts ranging from studios up to three-bedroom, two-bath units over 2,000 square feet, and all with full kitchens. I stayed in a one-bedroom loft on Middle Street that offered 600 square feet of living space with tall arched windows, hardwood floors, a king bed, a kitchen well-stocked for cooking or reheating leftovers, and a large bathroom with a walk-in shower, rainfall showerhead, and Lather toiletries. Read my full review of The Docent’s Collection here.
