Discover These Captivating Spots in Portland, Maine.

Here’s the thing about Portland: No one here is trying to impress you with trendy-this or glam-that. Sure, they want you to be here, to share their love of creative food and proud history of agriculture, craftsmanship, and maritime history. But at the end of the day, what fuels this proud little city is that the best things to do in Portland remain so true to its identity. From epic sailing trips and historic homes to funky boutiques full of artisanal wares and independent locavore restaurants, here are some of the best ways to discover the town. Read on for what to do when you’re in Portland, Maine.

1. Casco Bay Islands

Though beaches are few and far between in Portland, shorelines abound in the nearby Casco Bay Islands. The Casco Bay Islands are a group of islands located off the coast of Portland, six of which are accessible by ferry year-round. Each island has its own personality, history, attractions, and activities. Cliff Island, one of the smallest Casco Bay Islands, is home to only 60 residents year-round and is the only year-round island that features unpaved roads and as such, cars are seldom used. Cars aren’t allowed, so walking, biking, or getting around on golf carts are the modes of transportation. You’ll find plenty of beaches on this isle, specifically the stunning Diamond Cove, as well as a small museum, a bowling alley, and tennis courts. You can make a weekend of it and stay at the Inn at Diamond Cove, which has a host of activities and excellent dining options.  

2. Old Port

Old Port is without a doubt the beating heart of Portland. This downtown neighborhood is considered the city’s center and bustles with things to do left and right, all the while gracefully maintaining its historical facade. The area is lined with cobblestone streets and 19th-century warehouses, and with the wharf just steps away on Commercial Street, the city’s heydays as a world-renowned port town are easily felt. Tourists can benefit from ferries and cruise experiences as well as the delectable catches that dock there daily. Away from the waterfront, travelers will find plenty of options to sustain and entertain. Some of the city’s most popular restaurants can be found in Old Port. 

3. Portland Museum of Arts

For such a small city, Portland houses some pretty big names in its art museum. Andy Warhol, Claude Monet, and Winslow Homer are among the icons showcased within the Portland Museum of Art. Along with some of the greats, the museum features an extensive collection of American, European, and contemporary works, as well as pieces from Maine artists. Paintings abound, but you’ll also find photographs, sketches, pottery, furniture, ornate silverware, sculptures and so much more. Recent travelers were impressed with the Portland Museum of Art, expressing their delight at its collections. Visitors enjoyed the diversity of styles featured, from French impressionists to American classics, as well as the numerous works displayed, with many saying they could have easily explored the premises all day.

4. Eastern Promenade

Portland’s waterfront is at its most picturesque at the Eastern Promenade. Beloved by locals, the Eastern Promenade is a 68-acre waterfront park located on a stretch of land separating Back Cove from the Fore River. The park offers trails, beaches, and plenty of grassy areas to simply kick back and unwind. To make the most of your visit, take a stroll along the 2-mile-long Eastern Promenade Trail, which starts in the heart of the Old Port. Once an old rail line, the Eastern Promenade Trail takes visitors away from the excitement of the city’s center to the rocky banks of Fort Allen Park. Once you’ve gotten your fill of the scenic shoreline, consider a climb up the park’s grassy hills for sweeping views of the bay, as well as the islands and boats that dot its deep blue waters. 

5. Portland Farmer’s Market

Supporting local agriculture has been a part of Maine’s way of life for as long as anyone can remember, and Portland’s farmers’ market is one of the best places to embrace that mission. Here 40-plus growers, cheesemakers, beekeepers, berry farmers, bakers, wildflower florists, and far more set up stalls here twice a week in the summer and fall (on Saturdays at the Deering Oaks Park location and on Wednesdays at Monument Square) and once a week during winter (on Saturdays on Stevens Avenue).