Best Things to Do in Portland, Maine

Talk about being the most all-American, small-town diner that there is. Since 1991, this waterfront diner has been serving locals and tourists alike with food such as hearty breakfast meals and a quarter-pound of fresh lobster meat. Fight all you want over whether mayo or melted butter is better, but don’t forget to order the “Hobson’s Wharf.” 

It’s Maine, you’re gonna try some Lobster. This shop is the Five Guys of the lobster world, in both design and menu. At Highroller, you can get the crustacean on a roll, a stick, in a grilled cheese or even in a BLT. Try their “lobster flight” if you’re feeling particularly adventurous.

If you’re looking for something more upscale, then we’re serving a suggested plate of the Old Port Sea Grill and Raw Bar. Since 2002, the restaurant has been a classic hit on Portland’s dining landscape. Their menu features an extensive line of fresh raw oysters, with highlights being the local monkfish and the chickpea-covered local hake. Oh, and the grilled Faroe Island salmon! Also, notice when first walking in, you’ll see a classy lounge area with a 250-gallon fish tank and concrete bar. 

If you’re looking for a step up from fast food, this lobster shack sits on the water and sells fried seafood of all kinds to nibble on. Get your oysters, clams, fish and calamari in bite-size pieces, or try their fried pickles and popcorn chicken.

Eventide describes itself as “a revival of the great American oyster bar.” This is the kind of place to go if you want to sit at the actual raw bar and sip a cocktail amongst the open shells. Whether you go for oysters, soup or fish, you can expect the plating to be a step up from a lobster shack, the dishes here definitely get points for artistic arrangement (typically in a row, adorned with Jackson Pollock-esc splatters of sauce).

A family-owned business since 1994, Shipyard is one of the forerunners of Maine’s modern craft beer brewing. 

One of the most familiar breweries in town; try their Belgian-modeled beer or the infamous Allagash White. 

One of the best places to get Maine’s signature fruit pie is Two Fats Cats Bakery. Right after some lobster tails, come to this low-key small shop on either Lancaster St. (newest location) or Broadway. 

Modern design aesthetics and beautifully arranged plates mix with the laid-back atmosphere of a bakery cafe. Bread & Friends doubles as a bakery if you’re looking to take something away, but has sit-down options for brunch and dinner.

With two locations in Portland, Tandem has peak indie coffee shop vibes. A bakery as well, it’s a great place to go for a morning breakfast run or to grab a larger assortment of baked goods. Plus, you can feel a little bit better about your environmental impact knowing the shop only uses single-origin coffee and all of their packaging is made from recycled materials. 

This Japanese bakery is maybe not what you’d expect to find in Maine, but its ingredients show off the array of fruit the state is known for. Inspired by European baking techniques and Japanese sensibilities, Norimoto’s baked goods are cycled through weekly based on seasonal Maine produce, so you can always find something new to try.

To get the full Portland waterfront experience, consider visiting this picturesque 68-acre waterfront park. Grab a beer and frolic along the two-mile park trail, passing along small beaches and patches of grassy areas and hills.

Off in Cape Elizabeth, Fort Williams was once an active military fort from the late 1870s to mid-1960s. What remains are the ashes of our country’s pride and the iconic Portland Head Light, the park’s most selfie-bombing spot. 

Casco Bay Islands are a group of islands, each with its own personality, and ferries are accessible year-round. 

In the heart of the art district, there sits the Portland Museum of Art, which houses iconic names such as Andy Warhol and Claude Monet. It has thousands of historic treasuries covering American and European riches, contemporary sculptures, photographs and more.

You haven’t seen all of Portland until you explore its rich past and European roots, starting with the Victoria Mansion. This National Historic Landmark was built in the mid-1800s as a tribute to Queen Victoria, and its architectural style was inspired by Italian villas.  Ninety percent of its original interiors are still alive and kickin’, but the mansion today now features hot running showers and an active AC. 

With its 19th-century cobblestone streets that swerve and slither at every corner, Old Port is basically the brain of Portland. As also the main tourist hub, Old Port is where ideas congregate over an overpriced soy latte, or where some of the city’s best restaurants, bars and shops are. Walk out of a posh boutique and end up in some funky, old brick building that hides a cozy speakeasy. Start around High Street to Franklin Street and make your way through, stopping every once in a while to smell the beer and fries (forget roses).

A quieter reflection of the city, Back Cove is a neighborhood next to the tidal basin on the north side of the city. It is the starting point going toward suburbia and popularly attracts runners to the Back Cove Trail. Colorfully dressed Victorian complexes and properly trimmed family homes line the low-key residential area. If you’re looking to rent an Airbnb for some months but want the quieter backend, then Back Cove is only a short drive from all the hustle and bustle.

If you’re in the mood for some good ol’ blues, join the local crowd at the Blue bar. In particular, every Saturday, they worship jazz with live jams. But, if you’re near Blue during the weekdays, you can still catch some open-mike nights, stand-up and tapas plates with Portland’s own twist. 

Once an abandoned railroad yard, Thompson’s Point is now one of the most popular outdoor areas to catch some live band music. Overlooking the Fore River, you might finally feel like a Mainer as you snack on more lobster rolls while catching one of the best sunset sightings.

What better and quirky way than to name your business Holy Donut, especially if it will draw dozens in line right out the door? Located on Park Avenue, Exchange Street, and Scarborough, you’ll get a taste of the holy spirit in over 18 different flavors. Try their maple bacon, dark chocolate with sea salt and toasted coconut. 

What might be better than daytime ferry trips and yelling like Tarzan on top of lighthouses? Consider boarding a schooner or sailing boat around the city. With three schooners under the National Register of Historic Places, you can get some breath of fresh, salty air that the congested inner city surely won’t give you.

Standing at seven stories high, this is the last remaining maritime signal tower in the U.S. Wander its old corridors back into Portland’s maritime history.

When shopping, Mainers love a good discount, and Renys is as traditional as their love for clam chowder and seafood. 

For casual cookers to gourmet chefs, explore the variety of free appetizing samples, regional dishes and even live cooking classes at this lively food shop.