Maine's Largest City Is A Lively Hub Of Waterfront Fun, Renowned Seafood, Old Walkable Streets, And Quirky Shops

Often playing the role of "big city" in books by Stephen King — which isn't saying much, in a state of small, rural towns — Portland is the heartbeat of arts, culture, and entertainment in southern Maine. A little less than 70,000 year-rounders call the city home; as is the case with many coastal towns, streets crowd with tourists in the summertime, when temperatures still rarely exceed 80 degrees, and a gentle breeze floats off the harbor. Its relative proximity to other major New England cities, like Boston and Portsmouth, has also contributed to Portland's popularity over the years. That, and its international jetport, which is located just 3 miles from downtown and has service from major airlines like American, Delta, and United.

It's common for Portland to rank among the country's top travel destinations in categories like outdoor recreation. Just a short drive away is Cape Elizabeth, where you'll find sites like Fort William Park, home to Maine's oldest lighthouse and plenty of hiking trails. You can also reserve tickets for day and sunset cruises past Portland's other picturesque lighthouses, schedule a charter fishing adventure, or explore the trails around the city's one and only natural waterfall. Really, there's no shortage of waterfront fun in Portland, where the harbor is full of lobster pots, and it's common to see boats, as well as cars parked in driveways.

Portland is also one of the best foodie destinations in America. It's known for its seafood in particular, and you're likely to spot lobster and raw oysters on local menus. Many of the city's restaurants and shops are concentrated in the Old Port District, a walkable neighborhood where there are cobblestone streets and buildings dating back to the mid-19th century. Popular eateries in the area include The Holy Donut, which is known for its potato dough, and Central Provisions, an upscale restaurant with small plates and an outdoor patio.

For a more curated dining experience, get tickets for a culinary walking tour; the guides will also share a few local history facts along the way. Stops change regularly depending on the season (tickets are available year-round), but you can usually expect lobster, New England clam chowder, and locally brewed beer. It costs about $150 per person. If you're more history buff than foodie, check out one of Portland's historical walking tours, which are considerably more affordable at around $40 per person; you'll learn about the literary figures that once called the city home, Revolutionary War and Civil War history, and more.

While you're here, make sure to shop around at Portland's eclectic mix of stores. There are old-fashioned souvenir and gift shops, art galleries, and lots of clothing boutiques. The best time to travel to Maine might vary depending on your interests, but if you still need to shop for holiday gifts, Portland is an ideal wintertime option.

During peak tourist season — between July and August — overnight stays in Portland, Maine, can get pricey. Rooms at the Longfellow Hotel on Congress Street, for instance, can cost you over $700. That being said, there are always more affordable options to choose from. Visitors will find a long list of quaint bed and breakfasts, motels, and rental cottages. You'll find some vacation rentals in historic downtown homes, within walking distance of Portland's best restaurants. There are also modern penthouses with sweeping views of the harbor, and shingled cottages surrounded by perennial gardens.

Or, opt for an off-the-beaten-path destination just outside the city. You can escape Portland crowds in Cape Elizabeth, just 20 minutes away, or check out Old Orchard Beach, which is home to New England's only beachfront amusement park. Amtrak's Downeaster train runs through town on its way to Portland, Freeport (home of the very first LL Bean store), and beyond. If you're on a budget and booking last-minute, snap up a Greyhound bus ticket between Boston and Portland for just $20, even cheaper than filling up the tank.