Portland ME: Culinary Capital, Victorian Port & Downeast Islands

A mile-long park on the granite bluff above Portland Harbor, with views of Casco Bay's Calendar Islands and the White Mountains on the western horizon. The Eastern Promenade Trail runs 2.1 miles along the waterfront below the bluff; the 1895 Fort Allen Park at the promontory point has Civil War coastal fortifications visible from the walking path.

Maine's largest art museum, anchored by its landmark 1983 Charles Shipman Payson Building designed by I.M. Pei and Henry Cobb, bringing a modernist counterpoint to the Victorian surroundings of Portland's arts district. The permanent collection traces the development of American landscape painting through the Maine artists: Winslow Homer's studio in Prouts Neck is managed by the museum, and the Homer galleries hold the largest collection of his work outside the Smithsonian.

The mile-long commercial street connecting the museum to the East End has been transformed over 20 years into New England's most concentrated arts district outside Boston — independent galleries, design studios, vinyl record shops, and the Portland Observatory (1807) on Munjoy Hill at the street's east end. The Observatory is the only remaining marine signal tower in the US.

A 17-minute ferry from Portland's Custom House Wharf to Peaks Island — the most accessible of Casco Bay's Calendar Islands, with a 3-mile perimeter road walkable in 90 minutes. The island has 900 year-round residents; the back shore faces the open Atlantic and has a particular desolate granite character at low tide. The Civil War museum in the old Fifth Maine Regiment Hall is the island's historical anchor.

The original L.L. Bean store in Freeport has operated 24 hours a day, 365 days a year since 1951 — the store never closes, in honor of a promise Leon Leonwood Bean made in 1917. The flagship building covers 220,000 square feet and includes a trout pond, a rock climbing wall, and displays of Bean's original canvas hunting boots. The town of Freeport grew around the store; 200 outlets now line Main Street.

A 1.2-mile trail to the open granite summit of Bradbury Mountain, 484 feet above the coastal plain — the view encompasses Casco Bay's 365 Calendar Islands and the White Mountains rising above the Maine hills. The park's 800 acres include 15 miles of mountain biking trails through mixed hardwood forest.

The most photographed village in Maine — a Federal and Greek Revival commercial core on Dock Square, with a tidal river, a working lobster harbor, and the Colonial Revival summer 'cottages' of the Walker's Point estate district. The Bush family compound on Walker's Point is visible from Ocean Avenue; the Kennebunkport Historical Society preserves 10 significant buildings in the village.

A seasonal seafood shack on the bridge over the Kennebunk River, operating from a 12-foot counter since 1968. The fried clams are Ipswich bellies, hand-shucked daily; the lobster roll is a quarter-pound of claw and knuckle meat on a toasted bun. The line runs around the building on summer afternoons — arrive before noon.

A 1.25-mile paved path along the granite headland above Ogunquit's Cove — the only public oceanfront walk of this character in Maine, with the Atlantic surf breaking directly below the path's edge. The walk from Perkins Cove to Ogunquit Beach passes 25 named viewpoints; the Perkins Cove end has lobster boats, galleries, and the Ogunquit Museum of American Art.

A 1953 modernist building on the edge of the Marginal Way cliff walk, holding one of the finest collections of early 20th-century American art in New England. Marsden Hartley, Robert Laurent, and Charles Woodbury — all of whom worked in Ogunquit in the 1920s — are represented in depth. The museum's position above the Atlantic, with floor-to-ceiling windows facing the surf, is itself a work of landscape design.