Portland Observatory

Portland is a small city that mixes urban sophistication with home-town friendliness. On the southern Maine coast, only a two-hour drive from Boston, Portland lies at the mouth of Casco Bay. With a population of about 65,000, this coastal hub has more than its share of interesting shops and great restaurants. Museums and theaters tend to be small and friendly. Art galleries and musical performances reflect the area’s wealth of creativity.

Most first-time visitors to Portland start their trip by exploring the Old Port, a collection of cobble-stoned streets lined with brick buildings packed with shops, restaurants, boutiques, bakeries and coffee shops.

If the weather’s fine, you can take a stroll along East End beach and gaze out across Casco Bay. A trail connects the Old Port, from Commercial Street, along the harbor to East End Beach. If you’re feeling strong, keep going: the trail connects to the Back Cove trail, a 3.25-mile path that circles the picturesque bay that separates the downtown peninsula from the rest of the city.

Congress Street, Portland’s Main Street, is turning into a veritable arts district, anchored at the State Street end by the fine Portland Museum of Art and the Children’s Museum of Maine. Galleries, cafes, funky clothes stores and the Maine College of Art’s galleries and buildings line Congress and its side streets.

Portland is home to two minor league sports teams. In summer, the Portland Sea Dogs take up residence at Hadlock Field, and in winter, the Portland Pirates play at the Cumberland County Civic Center.

Also worth checking out: The Portland Observatory on Munjoy Hill, a ride on the Casco Bay Lines ferry, and the Farmer’s Market on Wednesdays in Monument Square. Just south of Portland, Cape Elizabeth is home to Portland Head Light, the most-photographed lighthouse in Maine.

Wharf Portland Maine