Misha's Guide to Portland
The Old Port
Portland’s Old Port neighborhood is the center of town and the most common tourist destination in the city. Its cobblestone streets are lined with cute shops, excellent restaurants (see below), and lively bars. I recommend starting in Monument Square at Longfellow Books, walking across the square onto Middle Street, and then turning on Exchange Street and walking all the way down to the piers on Commercial Street.
Eastern Promenade
On the eastern edge of Portland’s peninsula lies one of the most beautiful city parks in the United States. The Eastern Prom features a large lawn with a stunning view of Casco Bay and its many islands. There are tennis courts, basketball courts, and a walk along the water that will take you directly to Ocean Gateway, the site of our wedding. Go here in the middle of the day and eat at one of the many food trucks (my pick would be Mr. Tuna, recommended below).
Peaks Island
For a bit of a longer journey within the city limits, consider taking a ferry to Peaks Island. The ferry ride, which runs about 15 minutes, is a great way to see Casco Bay. Once on the island, you can cheaply rent bikes and take a swing around Seashore Ave, which has ocean views for miles and a number of cliffs and rock beaches to explore. You can also check out Battery Steele, an old and somewhat spooky World War Two fort. The island also features a number of bars, restaurants, and ice cream spots. See ferry times at the link.
Fort Williams Park / Two Lights State Park
Cape Elizabeth, a suburb about 15 minutes outside of Portland, is a beautiful ocean town strewn with cliffs, parks, and lighthouses. Fort Williams Park is the home of Portland Head Light, potentially the most iconic Maine landmark. Two Lights, as the name suggests, features two lighthouses, as well as a well-known lobster shack.
Scarborough Beach
If you are looking to slot in some beach time when you are in Portland, there are plenty of beaches to choose from. Most of them are in my hometown of Scarborough, and while they’re all great, I would recommend Scarborough Beach. Be warned – while Maine’s beaches may be more scenic than their rivals in Florida, the water is not quite as warm.
Rose Foods
Jewish deli featuring (in my opinion) Maine’s best bagels. Get the salami, egg, and cheese.
Becky's Diner
Landmark Maine diner on the water in downtown Portland. Get blueberry pancakes.
The Holy Donut
Famous potato donut spot with several locations across the Portland area, including one in the Old Port.
Duckfat
Excellent and popular lunch spot downtown featuring sandwiches, milkshakes, and duck fat fries. Prepare to wait for a table.
The Highroller Lobster Co.
One of many great choices for lobster rolls in the Old Port. Has a wide variety of types of roll, get one with mayonnaise as Mainers intended.
Cheese Louise Portland
Old Port sandwich spot specializing in grilled cheese.
OTTO
Iconic Portland pizza joint with locations across the city. It has since expanded to other cities and states, but I maintain the OG location on Congress Street is the best.
Mr. Tuna Food Truck
Sushi food truck on the Eastern Promenade. A spicy tuna roll in the park on a sunny day is tough to beat. (They also have a physical location downtown.)
Ramona's
Philadelphia-inspired hoagie joint in the East End on Washington Ave, near the Eastern Promenade. Enormous sandwiches. Get the Turkey Caesar.
Street & Co
Upscale seafood restaurant in the Old Port most famous for being the site of my first date with Ally. We got the lobster diavolo, but every single item on the menu is fantastic. Book in advance.
Scales
Newer seafood restaurant from the owners of Street and Co located on a pier with ocean views. Also excellent. Get the mussels, they’ll change your life. Also book in advance.
Pai Men Miyake
Ramen spot in the West End neighborhood, near where I went to high school. Go here if you like your ramen with a side of spicy tuna roll. Does not take reservations.
Yosaku
Long-standing sushi restaurant near the Old Port, which is likely my #1 most visited restaurant in Portland.
Terlingua
When it comes to New England’s food scene, Tex-mex barbecue is admittedly not the first thing that comes to mind. However, this place on Washington Ave rocks. Sit on the patio and get the brisket tacos and the street corn succotash.
Crispy Gai
Southeast Asian spot in the Old Port specializing in fried chicken. Everything on the menu is excellent. Does not take reservations.
ViA VECCHiA
Upscale Italian restaurant in the Old Port with great ambience for a date night. Get the calamari.
Sichuan Kitchen
No frills Sichuan place in the West End. Get the cold noodles and the double cooked pork.
Mount Desert Island Ice Cream
Ice cream place in the Old Port that is particularly meaningful to Ally and I since it has a location in Washington, DC. Its other locations are in Bar Harbor, Maine, and Matsumoto, Japan. We’re not sure what’s going with that either.
Gorgeous Gelato Portland
One of two dueling gelato places on Fore Street in the Old Port. Get the stracciatella or the hazelnut.
Standard Baking Co
Bakery owned by the proprietors of Street and Co and Scales, with a similar level of quality.
Bissell Brothers
My pick for Maine’s best brewery, known for its hazy IPAs. Their Swish Double IPA is my favorite beverage on this planet.
Austin Street / Rising Tide
Two breweries right next to each other in the Bayside neighborhood, with food trucks and ample outside seating. Austin Street will host our welcome drinks.
Novare Res Bier Cafe
Beer-focused bar in the Old Port with a lovely patio and a wide selection of beers from Maine and all over the world.
Blyth & Burrows
Excellent cocktail bar in the Old Port. Get the Ship Captain Crew or the Tom Yum Punch.
Sagamore Hill Lounge
Cocktail bar in the West End playing old movies and serving political themed drinks.
Top of the East
Bar at the top of the historic Eastland hotel (currently named the Portland Westin Harborview) which features the best panoramic view of Portland in the city.
Portland Zoo
My favorite bar in Portland. It has a large patio with a food truck, and is the definitive place to watch soccer in Portland. It’s also just down the street from our welcome drinks, so we recommend popping over for a drink after if you’re looking to continue your night.
Maps
Small bar in the Old Port decorated exactly as you would expect given the name.
Bayside Bowl Rooftop
Rooftop bar on top of Portland’s best bowling alley. Great at sunset for a view of Back Cove.
Bubba's Sulky Lounge
Legendary dance spot in Bayside featuring a light up dance floor, eclectic decor, and $3.50 Miller High Lifes.
Acadia National Park
About a two and a half hour drive up the coast from Portland is one of the nation’s most beautiful national parks. It lives up to the hype.
Morse Mountain to Seawall Beach
If you are split between wanting to spend your time in Maine hiking and going to the beach, I have great news for you. Seawall is a beautiful beach about an hour north of Portland that is only accessible via the Morse Mountain hike.
Sebago Lake
If you are more of a lake person than ocean person, Sebago Lake is an ideal spot, about 30-45 minutes outside of Portland depending on which side of the lake you are going to. Expect beaches with warmer water than their ocean counterparts and plenty of boating opportunities.
Freeport
Cute town 25 minutes north of Portland featuring outlet stores, Maine Beer Company, and LL Bean’s flagship store that is open 24 hours a day.
Tumbledown Mountain
My pick for the best day hike in Maine. About two and a half hours north of Portland, near the New Hampshire border, Tumbledown is a difficult hike that rewards you with beautiful views and a mountain lake near the summit.
