About This Trip
Portland punches well above its size. Two days covers Maine's rocky coastline, a historic lighthouse, and the islands of Casco Bay, all within reach of the country's most concentrated restaurant scene per capita.
Highlights
- Portland Head Light, most photographed lighthouse in America
- Casco Bay Islands kayak, paddle to Peaks Island and Great Diamond Island
- Eastern Promenade Trail, coastal path above the harbor
- Two Lights State Park, dramatic ocean ledges and tide pools
- Old Port waterfront, cobblestone streets, fish markets, craft cocktail bars
Day-by-Day Plan
Day 1
Portland Head Light + Casco Bay Kayak
- Fort Williams Park coastal walk, explore a Civil War fort with lighthouse views
- Casco Bay kayak from East End Beach, paddle among islands and working lobster boats
- Eastern Promenade Trail, 2-mile waterfront path above the harbor
Day 2
Islands + Two Lights State Park
- Peaks Island ferry + bike loop, 3-mile island circuit, beach coves, Civil War fort ruins
- Two Lights State Park, rocky ocean ledges, tide pools, Cape Elizabeth lighthouse
- Wolfe's Neck State Park (Freeport), coastal forest loop, osprey nesting platform