Exploring Portland, Maine

Big-City Attractions, Seaside-Town Charm

An important shipping and trading center since the 17th century, Portland is Maine’s largest city and one of the country’s busiest commercial ports. It also has the irresistible appeal of a salty New England seacoast burg. A massive in 1866 fire wiped out much of the town, but things were promptly rebuilt, creating the unique Victorian cityscape that is still largely intact today. Visitors can’t help but connect with both the city’s historic charm and its continued vibrancy, because the past and the present coexist here in almost unprecedented ways: cutting-edge boutiques sit next to traditional fishing markets in a cobblestone wharf district; some of the best and most progressive restaurants in New England—if not the country—occupy brick 19th-century industrial buildings.

Boaters will find the city and its environs particularly rewarding. Portland has a naturally deep harbor and is surrounded by glittering Casco Bay, which is dotted with islands to explore. Fishermen and sailors were the first to discover the area’s riches way back when—and the best way to tap into them is still aboard a sea-worthy craft.

WHAT TO DO

Wander Through Old Port The traditional maritime epicenter of Portland, and still a draw for tourists and locals alike. The area’s narrow waterfront streets are packed with shops, restaurants, bars, and working wharves. At the boutique Sea Bags (24 Custom House Wharf, 888-210-4244, seabags.com), pick up stylish but sturdy totes made from recycled sail cloth. The Old Port Candy Co. (422 Fore St., 207-772-0600, www.oldportcandyco.com) stocks house-made fudge and such nostalgic treats as Clark Bars and Pop Rocks.

Explore the Arts Portland’s thriving Arts District is full of well-established institutions and funky galleries. The highly regarded Portland Museum of Art (7 Congress Sq., 207-775-6148, portlandmuseum.org) has a wing designed by I. M. Pei and works by such prominent New England artists as Winslow Homer and Andrew Wyeth. The International Cryptozoology Museum (661 Congress St., www.cryptozoologymuseum.com/) is a quirky homage to such legendary creatures as Big Foot and the Feejee Mermaid. The Maine Potters Market (376 Fore St., 207-774-1633, www.mainepottersmarket.com) is a 25-year-old cooperative showcasing the work of 15 skilled potters and ceramicists.

Climb a Watch Tower The Portland Observatory is a shingled 1807 tower atop the city’s tallest hill. It was originally used to spot ships coming into the harbor, and now affords fine panoramic views of Casco Bay. When flags are flapping from the cupola, the tower is open to the public. (138 Congress St., 207/774-5561, www.portlandlandmarks.org/observatory)

Catch a Baseball Game The Portland Sea Dogs are a Double-A affiliate of the Boston Red Sox and their games draw an enthusiastic, family-friendly crowd to downtown’s Hadlock Field. It’s hard to find a better way to spend an afternoon than cheering on the home team, hot dog and Cracker Jacks in hand. (271 Park Ave., 207-879-9500, www.portlandseadogs.com)

Tour a Historic House Several of Portland’s grande-dame manses are now open to the public. The 1786 Wadsworth-Longfellow House (489 Congress St., 207-774-1822, mainehistory.org) served as George Washington’s headquarters while in the area and was the boyhood home of poet Henry Wadsworth Longfellow. The 1860 Victoria Mansion (109 Danforth St., 207-772-4841, www.victoriamansion.org) was one of the most opulent brownstones of its day and has been meticulously restored.

Mosey Along the Waterfront The tranquil Munjoy Hill neighborhood, in the city’s northern section, is ringed by the Eastern Promenade, an oceanfront pathway with sweeping views of Casco Bay.

Go Ride a Bike There are a bunch of great biking trails in and around town—the organization Portland Trails (305 Commercial St., 207-775-2411, trails.org) can point you in the right direction. Rent wheels downtown at Cycle Mania (59 Federal St., 207-774-2933, www.cyclemania1.com).

Island Hop Two-mile-long Peaks Island is a quaint refuge within the city limits, just three miles across Casco Bay from downtown. Take the 20-minute ferry ride over, circle the isle by walking along the seaside road, grab an ice cream cone at the dock, then board the ferry back to the mainland. (Portland Ferry Terminal at 56 Commercial St., 207-774-7871, www.cascobaylines.com)

WHERE TO EAT

Bresca Chef Krista Kern Desjarlais turns out thoughtful and thoroughly delicious seasonal dishes inspired by Italy and France--sea-urchin linguini with basil and mint, honey-glazed duck breast with pickled peach and frisee. The menu changes often, the wine list highlights small-batch bottlings, and the dining room is intimate and inviting. (111 Middle St., 207-772-1004, www.restaurantbresca.com)

Duckfat Casual spot with stellar sandwiches (think: homemade meatloaf with pickled onions and horseradish mayo), scrumptious milkshakes (the ice cream comes straight from nearby Smiling Hill Farm), and to-die for french fries—cooked in, yes, duck fat. 43 Middle St., 207-774-8080, duckfat.com

Evangeline The relaxed-but-chic vibe is immediately welcoming, and chef Erik Desjalais’s assured bistro-style cooking—roast quail with caramelized onions, sweetbreads with braised endive and bacon—means the place holds its own in the town’s competitive dining scene. (190 State St., 207-791-2800, www.restaurantevangeline.com)

Fore Street James Beard Award-winning chef Sam Hayward helped kick-start Portland’s unlikely prominence as a foodie haven. Pristine ingredients such as hand-harvested scallops and island-raised lamb are rigorously sourced from local farmers, fishermen, and purveyors, then prepared in ways that let the flavors sing. The elegant space is spare yet warm and the bar is always lively. (288 Fore St., 207-775-2717, www.forestreet.biz)

Hugo's Like his ultra-talented colleagues around town, James Beard Award-winning chef Rob Evans buys locally and thinks seasonally, but he also injects his food with a bit more whimsy and molecular-gastronomy flair than his counterparts: dashi-simmered beef short ribs with seaweed slaw and shitake mushrooms, spice-roasted monkish and oxtail peirogi with heirloom carrots. (88 Middle St., 207-774-8538, www.hugos.net)

Portland Lobster Co. Waterfront eatery that’s the locals’ favorite for all things lobster—lobster bisque, lobster rolls, whole steamed lobsters. They make excellent versions of all the other New England standbys too, including fried clam bellies and bacon-studded chowder. Regional microbrew beers are on tap and there’s live music most nights of the week. (180 Commercial St., 207-775-2112, www.portlandlobstercompany.com)

WHERE TO DOCK

DiMillo's Old Port Marina In the heart of the Old Port district, with easy, deep-water access from the ocean and anchorage for transients up to 250 feet. Amenities include a laundry service, cable TV, a pump-out station, and a courtesy van. (1 Long Wharf, 207-773-7632, www.dimillos.com)

For more information on Portland, visit the Greater Portland Convention & Visitors Bureau at www.visitportland.com.

Kennbunkport

Located approximately 25 miles south of Portland, Kennebunkport is worth a side trip from Portland. This quaint town became well-known as the family retreat for the Bush Family and is now a popular resort destination on its own with small shops, art galleries, seafood restaurants, hotels, inns, and bed & breakfasts. Historically a fishing village, the history of Kennebunk, as it is known, dates all the way back to the 1600's when it was a ship building mecca with five-masted ships and schooners making their way down the river on their way to the ocean. Stately mansions were built, many of which you can still see today as Inn’s or restored summer homes. Boaters will enjoy the small-town community spirit and the many marinas and facilities available.

Chicks Marina, the premier marina on the Kennebunk River, located just ½ mile from the ocean and short walk into the center of town, can take vessels up to 150 feet. (207-967-2782, www.chicksmarina.com).

Kennebunkport Marina, conveniently located in Kennebunkport’s beautiful protected harbor, 2/3 of a mile from the open Atlantic Ocean, and walking distance from dock square, offers a relaxed atmospherein a tranquil setting with convenient ammenities. (207-967-3411, www.kennebunkportmarina.com)