Portland Head Light & Fort Williams Park. Maine's oldest lighthouse, commissioned by George Washington in 1791, stands dramatically atop a headland at Fort Williams Park in Cape Elizabeth. The 90-acre park is free and open year-round, offering ocean views, walking trails, a maritime museum, and the beloved Bite Into Maine food truck.
Old Port Historic District. Portland's cobblestone-street heartbeat blends 19th-century brick warehouses with nationally acclaimed restaurants, boutique shops, and a genuine working waterfront alive with fishing boats and ferry traffic. Exchange Street, Fore Street, and Wharf Street pack more culinary talent per block than almost anywhere in…
Casco Bay Island Ferry & Peaks Island Day Trip. Casco Bay Lines runs year-round ferries to a scatter of islands just off Portland's shore; the 17-minute hop to Peaks Island rewards visitors with quiet lanes perfect for rented bikes, two public beaches, a Civil War-era fort, and sweeping views back toward the Portland skyline.
Portland Museum of Art. Founded in 1882 and Maine's largest public art institution, the PMA holds more than 18,000 works with a particular strength in Winslow Homer, Andrew Wyeth, and Maine Impressionism alongside Monet and Sargent. Friday evenings from 4–8 pm are free admission.
Allagash Brewing Company. One of America's most revered craft breweries, Allagash has been crafting Belgian-inspired beers since 1995 and is a Certified B Corp. Guided tours wind through the working brewhouse, and the family-friendly tasting room pours Allagash White — a coriander-and-orange-peel witbier that helped define American craft beer…
Eastern Promenade Trail. Designed in 1905 by the Olmsted Brothers, this 2.1-mile paved waterfront path traces the Casco Bay shoreline from the Old Port to Back Cove, connecting walkers, joggers, and cyclists to East End Beach, sweeping harbor panoramas, and some of the city's best sunrise views.
Victoria Mansion. A National Historic Landmark completed in 1858, this Italianate summer villa is widely regarded as the finest surviving example of Victorian-era interior design in the United States, with original painted ceilings, carved woodwork, and stained glass virtually untouched since the Gilded Age.
First Friday Art Walk. On the first Friday of every month from 5–8 pm, Portland's Arts District along Congress Street throws open gallery doors — free of charge — across museums, studios, and alternative art spaces. The Maine College of Art, Portland Museum of Art, and dozens of independent galleries all participate.
Top-rated tours & activities in Portland
The Real Portland Tour: City and 3 Lighthouses Historical Tour with a Real Local — 5.0★ (1,614 reviews)
Portland City and Lighthouse Tour — 4.8★ (1,148 reviews)
Harbor Lights and Sights Cruise — 4.8★ (770 reviews)
Port City Lights Cruise — 4.8★ (293 reviews)
Old Port "Seafood Lovers" Walking Lunch Tour in Portland, Maine — 4.8★ (150 reviews)
Sunset Windjammer Cruise Along the Coast of Portland Maine — 4.7★ (175 reviews)
Half Day Kayak Rental on Sebago Lake — 5.0★ (21 reviews)
Portland Explorer | Maine History, Culture, & 3 Lighthouses Tour — 4.9★ (979 reviews)
The Real Portland Tour: City and 3 Lighthouses Historical Tour with a Real Local — 5.0★ (1,614 reviews)
Portland City and Lighthouse Tour — 4.8★ (1,148 reviews)
Harbor Lights and Sights Cruise — 4.8★ (770 reviews)
Port City Lights Cruise — 4.8★ (293 reviews)
Old Port "Seafood Lovers" Walking Lunch Tour in Portland, Maine — 4.8★ (150 reviews)
Sunset Windjammer Cruise Along the Coast of Portland Maine — 4.7★ (175 reviews)
Half Day Kayak Rental on Sebago Lake — 5.0★ (21 reviews)
Portland Explorer | Maine History, Culture, & 3 Lighthouses Tour — 4.9★ (979 reviews)