I’ve been going to Portland, Maine almost as long as I’ve been alive. Twice a year we would visit my grandparents in Kezar Falls, about 40 miles west of Portland. Then, we would always accompany them on what they deemed a big shopping trip to this charming coastal city that many mistakenly think is the capital of Maine. It’s not — that’s Augusta.
Most times we would visit the Maine Mall, which was a big deal for my apple-farming grandparents. If you wanted to shop in a department store and weren’t heading to Filene’s in Boston, then JCPenney or Sears at the mall was it.
What to do in Portland, Maine
However, there is much more to Portland than visiting the mall. So, whether you’re a local planning a day trip, or you’re from away and want a weekend getaway or a more extended visit, here are some of the best things to do and places to go in Portland.
Portland Head Light
The Portland Head Light is an iconic lighthouse located in Cape Elizabeth, just a short drive from downtown Portland. The lighthouse was commissioned by President George Washington in 1787 and was completed in 1791. We wrote about it in our article on the history of Maine’s lighthouses.
In addition to its historical significance, it offers breathtaking panoramic views of the rugged Maine coastline and the Atlantic Ocean. The surrounding Fort Williams Park provides ample opportunities for picnics, scenic walks and enjoying the coastal beauty.
Also, it’s a great place to get a meal, believe it or not. The Bite Into Maine Food Truck is away from the other food trucks closer to the Head Light — Cousin’s Lobster and a gelato food truck the last time we were there. From Bite Into Maine we’ll get a Maine lobster roll and local soda, and enjoy the view of the nearby lighthouse and ocean.
Old Port
The Old Port is a historic and vibrant district located in the heart of Portland, Maine. It’s one of the city’s most popular and picturesque areas, known for its cobblestone streets, charming brick buildings, boutique shops, excellent dining options and lively atmosphere.
During cruise season, it’s where the ships let off passengers to spend the day shopping and eating. So, if you’re not a fan of crowds, you may want to visit the Old Port during the shoulder season. Then, there will be fewer people around.
As the sun sets, the Old Port comes alive with a vibrant nightlife scene. If you’ve ever been to the South Side of Pittsburgh or South Street in Philadelphia, that’s what you can expect at the bars along Commercial Street on the waterfront You’ll find a variety of bars, pubs and clubs where you can enjoy live music, craft cocktails and local beers. It’s a popular destination for both locals and visitors looking to have a good time.
If you’re hungry and want a great view, we recommend Luke’s Lobster. Sure, it might be a bit of a tourist trap but the food is worth it. Also, they’re dog-friendly. We took our pups Oscar and Sadie with us.
Finally, Portland and Old Port still have working wharfs so the food you eat could have come in off a boat earlier in the day.
Harbor cruise
A harbor cruise in Portland, Maine, is a fantastic way to experience the city’s coastal beauty, explore its islands and learn about its maritime history. Enjoy breathtaking scenic views of the coastline, Casco Bay and the surrounding islands. Don’t forget your healthy snacks for this trip.
The Maine coast is known for its rugged beauty, and you’ll get to see it from a unique perspective on the water. Casco Bay is home to several picturesque lighthouses, including:
- Portland Head Light
- Spring Point Ledge Light
- Ram Island Ledge Light
These are among the notable ones you might see during your cruise.
Food scene
Portland, Maine, boasts a thriving food scene renowned for its fresh seafood, especially lobster rolls, and a strong focus on farm-to-table dining. The city’s coastal location ensures a steady supply of high-quality seafood, which is featured in various dishes like clam chowder and seafood platters. Craft beer and distilleries are also prominent in Portland, offering an impressive selection of locally brewed beers and craft spirits. In fact, if you’re looking to plan a beer vacation, Portland is the perfect place to do it.
“When in Portland, a lobster roll every day is a must for me,” says Susannah Brinkley Henry, Feast + West. “My favorites are the ones at Eventide, which is great for a night out, and High Roller, a more casual joint. There’s not much better than a fresh, luscious lobster roll straight from the source. For dessert, don’t forget to try a whoopie pie — they’re a Maine delicacy.”
I agree with Susannah about Eventide. Even though we had to wait over an hour for a table — don’t worry; they take your phone number and will text you — it was worth the wait. On our last visit, we pretty much got dinner and a show. That’s because we sat at the bar overlooking the oyster shuckers.
Art galleries
Portland has a thriving arts scene. Visit galleries like the Portland Museum of Art or the Portland Art Gallery.
Also, from time to time, you can enjoy free admission at the Portland Museum of Art. This includes through the Blue Star Museums program and Museums for All. The latter program is for SNAP EBT recipients.
Portland observatory
The Portland Observatory is a historic maritime signal tower that was constructed in 1807 atop Munjoy Hill. The observatory has been meticulously restored and preserved as a museum, offering guided tours that delve into its maritime history and providing visitors with the opportunity to ascend to the top for breathtaking vistas of the harbor and surrounding areas.
Another great way to gaze at the stars: the Southworth Planetarium, on the Portland campus of the University of Southern Maine. It’s one of the stops we recommend when you’re looking for indoor things to do on a rainy day.
Casco Bay Islands
Casco Bay Islands are located just off the coast of Portland. Peaks Island, the largest and most accessible, boasts scenic beaches and a vibrant artist community. Great Diamond Island features historic Fort McKinley and Victorian-era homes, while Long Island offers sandy shores and hiking trails. Chebeague Island entices travel entusiasts with its charming village and historic inns.
Bailey Island is famous for its Cribstone Bridge and coastal beauty. Little Diamond Island provides a quiet escape, and House Island showcases military history. Cliff Island offers rustic serenity as the smallest year-round island. Ferries make these unique destinations easily reachable, providing opportunities for relaxation, exploration and outdoor adventures, all while immersing visitors in the natural beauty and history of the region.
International Cryptozoology Museum
The International Cryptozoology Museum is a unique and intriguing museum that focuses on cryptozoology. Cryptozoology is the study of hidden or undiscovered animals, often focusing on creatures that exist in folklore, myth or have limited scientific evidence supporting their existence. The museum is dedicated to the exploration and documentation of these mysterious and elusive creatures.
Maine Narrow Gauge Railroad
The Maine Narrow Gauge Railroad Co. & Museum is a historical attraction dedicated to narrow gauge railroading’s history in the state. It offers scenic train rides along the Casco Bay waterfront. Relax in one of the beautiful historic train cars while you take in the amazing scenery. On-board narration provides history about the sights along the route, as well as Maine railroading history.
During the holiday season, you can ride the Portland, Maine version of the Polar Express train. It’s a Maine Narrow Gauge Railroad specialty.
These activities showcase the diverse attractions and experiences that Portland, Maine, has to offer, from its historic sites to its natural beauty and vibrant food scene. Portland has many campgrounds nearby, which makes this a great travel spot for those who live the van life or RV lifestyle.
Portions of this article originally appeared on Food Drink Life.