Essentials

Restaurants

America’s "Foodiest Small Town" is how one magazine described Portland, which is practically bursting at the seams with fabulous restaurants to rival those of a major metropolis. It's worth it to splurge and try as many as possible while visiting. Fresh seafood, including the famous Maine lobster, is still popular and prevalent, but it is being served up in unexpected ways that are a far cry from the usual bib and butter. There is a broad spectrum of cuisines to be enjoyed, and many chefs are pushing the envelope in their reinventions of traditional culinary idioms. More and more restaurants are using local meats, seafood, and organic produce as much as possible; changing menus reflect what is available in the region at the moment. Even the many excellent food trucks that have popped up across the city—several of which remain open in the off-season—reflect this trend. As sophisticated as many of these establishments have become in the way of food and service, the atmosphere is generally laid-back; with a few exceptions, you can leave your jacket and tie at home—just not your appetite. Smoking is banned in all restaurants, taverns, and bars in Maine.

Hotels

As Portland's popularity as a vacation destination has increased, so have its options for overnight visitors. Though several large hotels—geared toward high-tech, amenity-obsessed guests—have been built in the Old Port, they have in no way diminished the success of smaller, more intimate lodgings. Inns and B&Bs have taken up residence throughout the West End, often giving new life to the grand mansions of Portland's wealthy 19th-century merchants. For the least expensive accommodations, you'll find chain hotels near the interstate and the airport.

Expect to pay at least $150 or so per night for a pleasant room (often with complimentary breakfast) within walking distance of the Old Port during high season, and more than $400 for the most luxurious of suites. At the height of summer, many places are booked; make reservations well in advance, and ask about off-season specials.

Nightlife

Portland's nightlife scene is largely centered on the bustling Old Port and a few smaller, artsy spots on Congress Street. There's a great emphasis on live music from local bands and pubs serving award-winning local microbrews. Several hip bars have cropped up, serving appetizers along with a full array of specialty wines and serious craft cocktails. Portland is a fairly sleepy city after midnight, but you can usually find a couple of bars and restaurants open, even after the clock strikes 12.

Performing Arts

Art galleries and studios have spread throughout the city, infusing many beautiful, old abandoned buildings and shops with new life. Many are concentrated along the Congress Street downtown corridor; others are hidden amid the boutiques and restaurants of the Old Port and the East End. A great way to get acquainted with the city's artists is to participate in the First Friday Art Walk, a free self-guided tour of galleries, museums, and alternative-art venues that happens—you guessed it—on the first Friday of each month.

Shopping

Exchange Street is great for arts and crafts and boutique browsing, while Commercial Street caters to the souvenir hound—gift shops are packed with nautical items, and lobster and moose emblems are emblazoned on everything from T-shirts to shot glasses.

Activities

When the weather's good, everyone in Portland heads outside, whether for boating on the water, lounging on a beach, or walking and biking the promenades. There are also many green spaces nearby Portland, including Crescent Beach State Park, Two Lights State Park, and Fort Williams Park, home to Portland Head Light. All are on the coast south of the city in suburban Cape Elizabeth and offer walking trails, picnic facilities, and water access.

Various Portland-based skippers offer whale-, dolphin-, and seal-watching cruises; excursions to lighthouses and islands; and fishing and lobstering trips. Board the ferry to see nearby islands. Self-navigators can rent kayaks or canoes.