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Portland, Maine is a charming New England city, perfect for a day trip from Boston. As the most populous city in Maine, Portland is home to an active marine industry, and still supports fishing and commercial shipping today. Bon Appetit even named Portland their 2018 Restaurant City of the Year, ranking it higher than New York or L.A.
Lucky for us, there are an abundance of Portland Maine things to do, especially if you’re heading there for a day trip!
Fun things to do in Portland Maine are in abundance, and in addition to the outstanding food scene, there are vibrant shops, parks, museums, festivals, beaches, and outdoor spaces to delight visitors of any age.
We headed up to Portland on Veterans Day in mid-November, and it was still a great time to head north of Boston. The air was definitely crisp, but blue skies were in abundance. It was cold enough to need a coat and gloves, but the sun was shining all day.
It takes about 2 hours to drive to Portland from Boston. You’ll take 93 North and drive past Portsmouth, New Hampshire, another charming New England town. If you decide to make it a weekend trip, a Portsmouth and Portland combo would be perfect for two days.
There are tons of cool things to do in Portland Maine year-round, but I am going to outline our one-day itinerary, which was a great way to spend one day in Portland. For a full list of fun things to do in Portland Maine and many Maine points of interest, visit the visitportland.com website to find a local events calendar, things to do, a full list of restaurants, and more!
Onto the itinerary!
After getting off the road, we started with breakfast at the Portland Pottery Cafe. The cafe is located in the East End and offers a variety of breakfast items, soups, sandwiches, pastries, and more. On the chilly November morning, we decided to pop in and share some of their homemade zucchini bread, coffee, and an omelette. It was the perfect way to start our day trip in Portland!
All of the food was served on (I assume) handmade plates and mugs of pottery made in the store. See, the cafe is attached to a pottery store where you can take classes or purchase pottery-making supplies. There were a number of pottery items for sale, and you can browse around the cafe and shop area to see the items in progress and those that have been completed. I’d love to go back again to make some mugs or bowls.
After breakfast, head down to the Portland Eastern Promenade, where you can look out to the water where there are islands dotting the views in the distance. There’s a huge park with lots of green space, and a paved walking path along the gently sloping hill. The path is a former railroad trail and spans just over 2 miles.
There’s plenty of parking, so hop out and take a stroll. Thousands of people walk, swim, and run along the paths (I’ll pass on swimming in winter, thanks so much, though!).
Dogs are allowed on the grounds on-leash, and can go off leash during the off season. We brought our Shiloh Shepherd, who we caught mid-sneeze. Classic!
After your walk around the Promenade, head to the Portland Observatory, another fun thing to do in Portland, Maine. It’s one of the most well-recognized landmarks in the city, and it’s the last standing maritime signal tower in America! The National Historic Landmark was most active from the early 1800s-1900s to alert ship owners about the arrival of their vessels to port.
It’s open from late May through early October, so it was closed while we were there, but it was worth walking around the base of the tower to observe its rich red color and height.
After burning off some of those breakfast calories, we were ready for lunch. As I mentioned above, Portland is a foodie paradise, so there was an abundance of restaurants to choose from for lunch.
I figured that we should probably do seafood since anything caught would be local and fresh. Plus, isn’t New England known for oysters and lobster anyway?! When in Rome…
We headed over to Eventide Oyster Co. for lunch. Funnily enough, I have not been to their shop in the Boston Fenway neighborhood. I better change that soon, because their oysters were a 10/10. Mike Wiley and Andrew Taylor, chefs and co-owners of Eventide and their sister restaurants The Honey Paw and Hugo’s, are James Beard award-winners (it’s like the Oscar’s of the food industry and a high honor).
We tried one of their lobster rolls, an assorted half-dozen oysters, and the refreshing Pol Roger “Brut Rosé” Champagne. The attention to detail in the presentation, curation of the wine and beverage list, and enticing menu options clearly show why Eventide is one of the best restaurants in downtown Portland Maine.
After you’ve had your fill of wine and seafood, walk just a short ways to Commercial Street, the main shopping thoroughfare in Portland. Shopping along Commercial Street is definitely one of the most fun things to do in Portland Maine!
There are a number of quaint shops perfect for popping in and browsing or buying. My favorite shops are Company C for their quirky and elegant home furnishings and rugs and Danforth Pewter Company for their hand-crafted pewter lamps and gifts.
Just off Commercial Street you’ll find even more shops like Stonewall Kitchen for things like salsas and jams, The Salt Cellar for a “salt vault” session or Himalayan salt-infused bath products.
The whole shopping district is so charming and walkable, and you can get a feel for the local shops in an afternoon.
I ended up buying way too much at Danforth Pewter, including Christmas ornaments, key chains, and lapel pins. Everything there was just so cute and I loved that it’s all handmade in Vermont in the same way someone like Paul Revere might have used.
Just like lunch, it was almost impossible to pick a place for dinner since Portland is spoiled with dozens of outstanding restaurants. After much internal debate, Googling, and Yelping, I chose Fore Street, right in downtown Portland.
Unfortunately, I didn’t snag any pictures of it since the interior is quite dark and intimate. I didn’t want to be “that person” snapping Insta pics like a weirdo. So I hope you’ll take my word when I say Fore Street served up an amazing homemade dinner of comfort food classics reminiscent of a time when food warmed you up after a long day in the cold.
When you enter the restaurant, you’re met with leather seats and couches which face the street. The brick and wood bar area is cozy and warm, and you can sample some finely curated wines from around the world.
Their fresh bread is warm and filling, and I tried their local Maine chicken dinner, which was turned on the fire spit right in the restaurant. Served with greens, it was a warm and comforting way to end our fun day trip to Portland. The service at Fore Street was first-class, and our server made sure anything we needed was swiftly at the table.
If you’re looking for a fun day trip or weekend away, I’d highly recommend Portland Maine. There’s a wealth of things to do in Portland Maine from dining to shopping to outdoor recreation and more. If you’re visiting New England, five Portland a try–you won’t be disappointed!
Have you been to Portland? Leave a comment below with your favorite things to do below.
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