A narrow, cobblestoned lane in Old Port lined with merchants and history, Moulton Street leads you past buildings once central to Portland’s trade. It’s also one of the stops on the Portland Freedom Trail.

Located on the former site of Portland’s 19th-century marble post office building, this small urban green is now a shady, community gathering spot with a link to local history.

Across Exchange Street from Post Office Park, Tommy’s Park is a quaint plaza that offers benches under trees and views of mural-covered walls. It’s a calm pause amid the waterfront activity.

The ferry terminal where locals and visitors embark and return, giving views of islands, docks, and the sea’s shifting light. It’s both a transit hub and a scenic vantage.

Nestled at the corner of Fore and Moulton, the Mariner’s Church connects Portland’s maritime heritage with abolitionist history through its proximity to early printshops and meeting houses.

Commercial Street is a bustling waterfront strip of seafood shacks, boutique shops, and views of working piers. This is where Portland’s fishing past and present meet.

A stately building that once regulated trade and imports, the architecture of the United States Custom House recalls Portland’s deep ties to maritime commerce. It’s a solid landmark of federal presence amidst local hustle.

A floating restaurant and docked marina that blends nautical charm with delicious meals overlooking the bay. Here, you’ll find a unique way to dine with both water and history underfoot.

Once lined with warehouses, Wharf Street now brings you close to the waterfront where you can see the working docks, lobster boats, and taverns that tell the city’s working-shore story.

A small public square surrounded by historic buildings, offering benches, shade, and glimpses of old Portland architecture with little fanfare.

This historic meetinghouse on Federal and Pearl Streets has been the site of abolitionist speeches, anti-slavery riots, and Quaker worship for nearly two centuries.

An iconic waterfront restaurant and pub serving up fresh lobster rolls and seafood with views of working wharves. The Maine Lobsterman is a local flavor with a seafaring atmosphere.

Housed in a former newspaper printing facility, this boutique Press Hotel blends history, craftsmanship, and design. It’s also a good anchor point for exploring nearby Old Port streets.

Built in 1807, the octagonal tower of the Portland Observatory served as a maritime signal post, where watchmen helped ships entering Casco Bay avoid danger. The elevated deck now offers panoramic harbor views.