Cape Elizabeth is the home of Portland Head Light. Situated along the spectacular shores of Fort Williams Park. Photo via Shutterstock.

Best Things to Do in Portland, Maine

BY Fifty Grande Editors | April 1, 2021

Welcome to Fifty Grande’s Best of the U.S. Bucket List series. This is your one-stop travel guide to the best, most unique and quintessential experiences of a city, state or event. Want to know how to “do” Portland? We’ve got you covered. Curated by experts, vetted by in-the-know locals, this is all you need to have the best trip ever. If we’ve written a Bucket List, we recommend you go. If it’s on this list, it’s the best the city has to offer right now. Consider this your one-stop answer to “What are the best things to do in Portland, Maine?”

First thing first. The other Portland (Ore.) was named after this one. So, we’re talking about the original-flavor Portland in this guide — the low-key, no pretense, must-see cultural hub of Maine. The city has evolved over the past 25 years, but it still is the central casting equivalent of “quaint, charming New England town.” Its music and, more often, dining scenes have garnered national attention for up-and-coming brilliance, but locals know Portland has consistently punched above its weight class for a long time. In 1986, it became home to New England’s first craft brewery, long before the mini breweries were a thing in every corner of the country. Craft brews are still a reason to visit Maine, as are the iconic lighthouses, lush islands, a burgeoning arts scene and, of course, the amazing dining experiences. We highly recommend a visit to Portland. Here’s how to see it.

You’re Here for Lobster Rolls

Maine thrives on the marine industry, which pumps life into Portland’s soul, and lobster is what you should be eating as you stare out at all those lighthouses. For hours, one could debate whether mayo sauce should be mixed in with lobster claw or how naked the lobster meat should be, but it’s best if you find out for yourself. You won’t have a tough time finding them since, basically, they’re offered everywhere in the state.

Becky's Diner in Portland, Maine.
#1
Becky's Diner in Portland, Maine.

Becky’s Diner

390 Commercial St, Portland, ME, USA

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.” 

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Old Port
#2

Old Port Sea Grill And Raw Bar

93 Commercial St, Portland, ME, USA

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. 

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The Highroller Lobster Co. in Portland, Maine.
#3
The Highroller Lobster Co. in Portland, Maine.

The Highroller Lobster Co.

104 Exchange St, Portland, ME, USA

What started as two guys and a hot dog cart in 2015 is now a restaurant that serves some of New England’s finest lobster rolls on brioche buns. Fans also flock here for the BLT, Fried Lobby Pop and the Lobster Rangoons. 

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You’re Also Here for Beer..

As noted, Maine became home to New England’s first craft brewery, long before the mini breweries were a thing in every corner of the country. Lucky for us, now there’s tons to try.

Shipyard Brewing Company in Portland, Maine.
#4
Shipyard Brewing Company in Portland, Maine.

Shipyard Brewing Company

86 Newbury St, Portland, ME, USA

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

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#5

Allagash Brewing Co.

50 Industrial Way, Portland, ME, USA

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

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You’re Also, Also Here for Blueberry Pie

Maine is known for being a fertile-soil state with thriving wild blueberry bushes. Take advantage.

Two Fat Cats Bakery in Portland, Maine.
#6
Two Fat Cats Bakery in Portland, Maine.

Two Fat Cats Bakery

195 Lancaster St, Portland, ME, USA

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. 

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Spend a Day at a Park

Even if you’re stuffed with seafood and pies, don’t forget that Portland is one of Mother Nature’s favorite daughters. 

Eastern Promenade in Portland, Maine. Photo by Shutterstock.
#7
Eastern Promenade in Portland, Maine. Photo by Shutterstock.

Eastern Promenade

Eastern Promenade Trail, Eastern Promenade Trail, Portland, ME, USA

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.

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Fort Williams Park in Portland, Maine. Photo by Shutterstock.
#8
Fort Williams Park in Portland, Maine. Photo by Shutterstock.

Fort Williams Park

1000 Shore Road, Cape Elizabeth, ME, USA

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. 

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Casco Bay Islands in Portland, Maine. Photo by Shutterstock.
#9
Casco Bay Islands in Portland, Maine. Photo by Shutterstock.

Casco Bay Islands

56 Commercial St, Portland, ME, USA

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

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Say “Hello” to Victoria and Hipsters

As a bustling cultural and coastal city, Portland can amaze you with one hour of high-strung aristocrats in powder-white wigs and then an hour of remarkably groomed bandholz beards.

Portland Museum of Art in Portland, Maine. Photo by Shutterstock.
#10
Portland Museum of Art in Portland, Maine. Photo by Shutterstock.

Portland Museum of Art

Portland Museum of Art, 7 Congress Street, Portland, ME, USA

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.

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Victoria Mansion of Art in Portland, Maine. Photo by Shutterstock.
#11
Victoria Mansion of Art in Portland, Maine. Photo by Shutterstock.

Victoria Mansion

109 Danforth St, Portland, ME, USA

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. 

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Neighborhoods to Know

Roughly speaking, you can think of the city as the great divide between the progressive peninsula and the low-key inlanders. The following three neighborhoods reflect different aspects of Portland’s personality.

Old Port in Portland, Maine. Photo by Shutterstock.
#12
Old Port in Portland, Maine. Photo by Shutterstock.

Old Port

Exchange St, Portland, ME, USA

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).

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Back Cove in Portland, Maine. Photo by Shutterstock.
#13
Back Cove in Portland, Maine. Photo by Shutterstock.

Back Cove

Baxter Boulevard, Portland, ME, USA

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.

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Must-Try Live Music

Blue in Portland, Maine.
#14
Blue in Portland, Maine.

Blue

650a Congress St, Portland, ME, USA

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. 

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Thompson’s Point in Portland, Maine.
#15
Thompson’s Point in Portland, Maine.

Thompson’s Point

Thompsons Point Road, Portland, ME, USA

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.

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Cool and Unusual Things to Do

Holy Donut in Portland, Maine.
#16
Holy Donut in Portland, Maine.

Eat a Holy Donut

194 Park Ave, Portland, ME, USA

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. 

 

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Portland Schooner Co. in Portland, Maine.
#17
Portland Schooner Co. in Portland, Maine.

Portland Schooner Co.

56 Commercial Street, Portland, ME, USA

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.

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Portland Observatory in Portland, Maine. Photo by Shutterstock.
#18
Portland Observatory in Portland, Maine. Photo by Shutterstock.

Portland Observatory

138 Congress St, Portland, ME, USA

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.

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Fun Stores

Due to its strategic location near the sea, Portland holds a true and rich history of oceanic trades and a heavy influx of immigrant labor. Today, the city’s shopping options greatly reflect its multicultural streets.

Renys in Portland, Maine. (with special guest, Bernie)
#19
Renys in Portland, Maine.

Renys

540 Congress St, Portland, ME, USA

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

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Stonewall Kitchen in Portland, Maine. Photo by Shutterstock.
#20
Stonewall Kitchen in Portland, Maine. Photo by Shutterstock.

Stonewall Kitchen

182 Middle St, Portland, ME, USA

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. 

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