Portland's Old Port is the part of the city visitors picture first: cobblestone streets sloping down to the working waterfront, 19th-century brick warehouses turned into shops and restaurants, and a density of good places to eat that is unusual for a city of its size. It is also easy to walk. Here is one way to spend an evening there, ending with dessert.
Start on Commercial Street
Commercial Street runs along the harbor and is the district's spine. Working piers still push out into Casco Bay from the south side, so a late-afternoon walk here comes with fishing boats, ferries and the smell of salt air. It's the best place to get your bearings before heading up the hill.
Climb Exchange and Fore Streets
The streets that run uphill from the water — Exchange, Fore, Market and Middle — are where the Old Port's brick architecture is at its best. Much of the district was rebuilt after the Great Fire of 1866, which is why so many of the buildings share a Victorian-era look. Independent shops, galleries and bars occupy the ground floors.
Dinner, then a walk
The Old Port has more restaurants per block than almost anywhere in New England, from raw bars to wood-fired kitchens. Whatever you choose, leave room: the point of this itinerary is that dessert happens somewhere else.
Finish on Middle Street
Middle Street runs parallel to Commercial, a couple of blocks up the hill. Gross Confection Bar sits at number 172, inside an 1883 bank building designed by Portland architect John Calvin Stevens, with arched brick rooms and high wooden beam ceilings. It opens at 5 pm Thursday through Sunday, seats parties under six on a first-come basis, and serves plated desserts with cocktails, wine and beer — which makes it a natural last stop.
Practical notes
- Parking: street parking in the Old Port is metered and tight on weekend evenings; the city garages nearby are the easier option.
- Footwear: cobblestones are charming and uneven. Flat shoes are the sensible choice.
- Weather: the harbor breeze drops the temperature after dark even in summer. Bring a layer.
- Timing: dessert bars fill up after nearby dinner services wind down, roughly 8–9 pm on Fridays and Saturdays. Arrive earlier for a quieter room.