Portland, Maine, delivers award-winning dining and year-round outdoor adventure in a small city by the sea.
Although it’s possible to catch sight of a sunbathing seal or a swimming dolphin while paddling the waters of Casco Bay in a kayak or atop a paddleboard, the chances of spotting marine wildlife are much greater aboard the Odyssey Whale Watch tour. The Odyssey takes passengers up to 20 miles out to sea, where humpback, finback, and minke whales, along with dolphins, sharks, and sea turtles frequently feed.
Galleries and art studios throughout Portland stay open late with exhibitions for the First Friday Art Walk each month, while the impressive Portland Museum of Art offers free admission every Friday evening. The PMA also owns and operates a museum from the home of one of Maine’s most famous artists, Winslow Homer, at nearby Prout’s Neck—the inspiration for many of his dramatic coastal landscapes.
Best Day Trip
The charming Midcoast towns of Camden, Rockland, and Rockport are less than two hours north of Portland by car and offer the classic small-town Maine experience, with countless hiking and boating options and fantastic dining options to boot.
Off the Beaten Path
Maine’s coastline is generally stark and rocky, making sandy beaches an in-demand contrast. Skip the crowds of Cape Elizabeth’s Crescent Beach State Park and opt for the smaller half of the same cove, Kettle Cove, next door. Make sure to check out the small trail along the cove’s outer cliff, watch lobster boats moor off the beach, and stay for a gorgeous southwestern-facing sunset. Afterward, treat yourself to a cone from nearby Kettle Cove Creamery.
Most Iconic Place
Make sure to see the iconic Portland Head Light—Maine’s oldest lighthouse—whether it’s from the water aboard a chartered boat or rented kayak or from the Cliff Walk Trail inside Fort Williams, with panoramic views of the sea.
Portland’s Washington Avenue has become a go-to spot for some of the city’s best new restaurants, bars, and distilleries. Hop from spot to spot within a three-block radius. Start with a round of oysters at The Shop, followed by natural wine at Drifters Wife, a bowl of pho at Cong Tu Bot, and finish the evening with beer and live music at Oxbow Brewing Company’s tasting room.
Accessible only by water, Fort Gorges rises literally out of the sea as a decommissioned military fort now owned by the city of Portland. Paddle to the island and explore the almost entirely unrestricted fort with views of Portland harbor, the Casco Bay Islands, and the Portland Head Light in the distance.
The Casco Bay Lines Mailboat Run winds visitors through five of the Casco Bay Islands on a real working boat, and is a unique, affordable way to experience Portland from the water on the country’s oldest continually run ferry service. Take the earlier mailboat and if you’re feeling adventurous, hop off to explore Long, Great Chebeqgue, or Cliff islands before catching a ride back on the second mailboat of the day.
Tommy’s Park on Exchange Street allows views of tourists, locals, restaurant-goers, shoppers, and gallery-hoppers in the center of Portland’s downtown Old Port neighborhood. From here, it’s also only a quick, two-block walk to Commercial Street to take in the sights of the city’s bustling working waterfront.
Best Outdoor Dining Experience
A meal under the stars from one of the picnic tables at The Well at Jordan’s Farm is not to be missed. While most of the ingredients are sourced from local Cape Elizabeth Farms, the experience of enjoying a delicious dinner outside on a farm is unforgettable.