A Weekend Guide to Portland, Maine

Portland, Maine. A bucket list city if I’ve ever been to one. From spotting a lobstaman in their yellow raincoats to enjoying a lobster roll to drinking blueberry beer and visiting a lighthouse … Portland was every bit a storybook as I thought it would be.

George and I have family who live in Boston, so we all decided to make the drive up to Portland for a night. It’s an easy 2 hour drive from Boston, although you could easily fly into Portland International Jetport (PWM). I’d suggest renting a car, since you’ll probably want to explore Cape Elizabeth (the most beautiful waterside homes + lighthouses).

Old Port is incredibly walkable and filled with fun shops, restaurants, and bars. You could bop along all weekend long, if you so pleased! We had about 30 hours total for our trip, so we packed a lot into the itinerary.

My personal bucketlist included …

See (and photograph) a lighthouse
Eat a lobster roll
Walk along the pier
Drink a local craft beer
Photograph a quintessential Portland building
BONUS: See a piece of the Berlin Wall

TO EAT

Note: If you’re traveling during peak seasons, I’d book your reservations ASAP. We made ours a month out from traveling.

Portland Lobster Co. This is a local and tourist fave! Not only do they have incredible seafood (lobstah), but they usually have fantastic live music. You could eat a meal and continue sipping on a pitcher of blueberry beer (YUM) for hours!

Luke’s Lobster. Located on the very end of a pier, Luke’s is a little bit removed from all the hustle and bustle, which is great when you don’t want to wait in lines. Try to grab a spot out on the deck or upstairs!

Via Vecchia. Incredible Italian food (their pizza - OMG) and craft cocktails. And every inch of this place is Insta worthy. Their back room has a darker, romantic, candlelit vibe while the front room is poppin!

Eventide. Pristine shellfish and a wine list to compliment, this is probably one of the most popular spots in town. The lucky ducks are able to snag a reservation, but don’t be surprised if you end up having to stand in line around the corner.

Central Provisions. Elevated tapas experience. Highly recommended by our family for a Spanish dinner!

Duck Fat. Some boast that Duck Fat has the best poutine in Maine. And maybe New England. Go for the french fries and sandwiches!

Forage Market. A great breakfast sandwich shop! You can call ahead to place your order, if you’d like to grab and go. They make all of the breads + bagels by hand!

Becky’s Diner. The parking lot is always full at Becky’s (or so we hear!). Classic diner feel in a classic gray wood shingled building. It was featured on the Food Network’s Diner’s, Drive Ins and Dives!

TO DRINK

Independent Ice Co. A trendy whiskey bar who manages to keep Blanton’s Bourbon in stock like a draft beer (unheard of!). They have hundreds of whiskey options to suit your fancy. Don’t worry if you’re not a whiskey drinker … they have plenty of delish cocktails on their menu! Dress up and cheers to the fact that you’re in Portland under a chandelier.

Portland Lobster Co. The live music and blueberry beer kept us on the outdoor patio for a good while! Defintiely be sure to try a blueberry beer while you’re in Maine!

Porthole. A rowdy spot right on their pier with great live music. Definitely a place to sit and enjoy a livlier crowd! #dranksssss

Blyth and Burrows. An upscale craft cocktail bar in Old Port.

Oxbow. Maine is famous for their craft beer scene. Owbox has an industrial feels to it, since they produce a lot of the beers on site! A great spot for a craft brewskie.

TO DO

Portland Head Light and Fort Williams Park. The most photographed lighthouse in the world and most iconic scene of Maine’s coastline. My jaw was constantly dropping to the ground - it’s just so gorgeous! Plus, you drive along the beautiful houses of Cape Elizabeth to get to the park.
See a piece of the Berlin Wall. Located next to Portland Lobster Co. - this piece of history is a unique attraction in the city.
Brewery Row (just outside the city). Craft beer, y’all!
Shopping in Old Port. Wander up and down the streets of Old Port popping in and out of shops. So many fun spots!
Shopping in Freeport. If you have extra time and can shop until you drop, Freeport would be a great option!

ROAD TRIP - KENNEBUNKPORT

If you have some extra time in Maine, I’d highly recommend making the trip to Kennebunkport for the day. The Bush Family complex is here! And Lordy, I see why. This little town is ADORABLE. We popped in and out of shops, enjoying walking along the waterfront, drank a cocktail on a sailboat (SO COOL) and snagged a beer at a local brewery.

Visit Dock Square
Sip a cocktail aboard The Spirit
Drink a brewskie on the deck of Batson River Brewing Co.

Maine (The Pine Tree State) is a beautiful place to explore. The natural beauty and jagged coastline were something to behold. Add it to your bucket list!