Greater Portland & Casco Bay

The historic seaport of Portland, Maine’s largest urban area, is perched on Casco Bay with its many island and coastal communities. This region is as celebrated for its arts and entertainment scene as it is for its walking and biking trails; as renowned for its local cuisine as for its access to outdoor adventures. Creative, exciting, happening, fun—it’s all here.

Portland’s Waterfront is a whirl of activity, as it has been for centuries. Walking trails, trolley tours, bay cruises, lobster-boat rides, historic schooners and island ferries all start here. Enjoy the many pubs and seafood restaurants. Walk the Eastern Prom Trail for stunning bay views.

The Old Port is a lively shopping district with cobblestone streets, boutiques, galleries and restaurants in renovated historic buildings. Stroll up Exchange Street, then head toward Monument Square for seasonal Farmers’ Markets and the childhood home of poet Henry Wadsworth Longfellow.

The Arts District, anchored by Portland Museum of Art, hosts galleries, antique shops, studios and theaters clustered around Congress Street. Visit the Children’s Museum of Maine, and don’t miss First Friday Art Walks.

Portland Freedom Trail takes you to 16 historic sites important in Maine's anti-slavery struggle. A self-guided tour helps you learn about our state's role in the Underground Railroad and the abolitionist movement.

Casco Bay - and the Calendar Islands that dot the bay - is Greater Portland’s maritime playground. Take a ferry to Peaks Island or cruise to Eagle Island to visit the summer estate of arctic explorer Admiral Robert E. Peary. Explore by kayak or sailboat or relax on a sunset cruise around the harbor.

Cape Elizabeth is home to Portland Head Light, Maine’s oldest lighthouse. The lamp of this much-photographed lighthouse was first lit in 1791. Portland Head Light sits in grassy Fort Williams Park, site of a former army post. Nearby is Two Lights State Park, where you can stop for another stunning coastal view. Head for sand and surf at Crescent Beach State Park or the beaches in nearby Scarborough.

South Portland sits across the harbor from Portland. This artsy city is known for its restaurants, bakeries, theaters and galleries. Visit Spring Point Light, at the end of a granite breakwater, or fly a kite at Bug Light Park.

Freeport is the home of world-famous L.L.Bean. It offers a lively mix of retail shops, factory outlets, restaurants, summer concerts and winter festivals. Take a shopping break and hike  the coastal trails at Wolfe’s Neck Woods State Park while watching for osprey and eagles. Or discover a truly unusual phenomenon, the Desert of Maine!

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"Don't Miss" Fairs & Festivals

• Maine Jewish Film Festival - Portland - March
• Old Port Festival - Portland - June
• Yarmouth Clam Festival - Yarmouth 
• Portland Chamber Music Festival - August
• Cumberland County Fair - Cumberland - September
• Harvest on the Harbor Food & Wine Festival - Portland - October
• Tree Lighting in Monument Square - Portland - November
• Sparkle Weekend - Freeport - December

So Much More to Do...

• Tour the Portland Observatory, the only remaining historic signal tower in the U.S.
• Stroll the nature trails at Gilsland Farm Audubon Center in Falmouth or explore the marsh at the Scarborough Marsh Audubon Center.
• Take a Great Portland Landmarks self-guided walking your of Portland's four major historic distrcits. 
• Eat! Portland was named America's "foodiest" small town by Bon Appetit magazine.
• Reserve your tickets for the symphony and the theater, or how about a semi-pro baseball, basketball or hockey game?
• See the world's largest revolving globe at Delorme headquarters in Yarmouth.