Walk, talk, and taste your way through historic Portland, Maine.

Quick Details

Map Marker Pickup & Drop-off Location: Old Port Spirits and Cigars

Adult Ages 21+
Private tour (includes gratuity) Up to 14 people


This leisurely walking tour allows you to visit and learn about notable Portland landmarks including numerous former brewery sites, the Workingmen’s Club, Mariners’ Church, the Seamen’s Club, and the working waterfront that was essential for importing and exporting of alcohol during times of prohibition.

As part of this historical journey, we will stop at these legendary Portland breweries:

Founded in 1994, Shipyard Brewing Company is one of the largest breweries in the State of Maine. The legendary partnership of Fred Forsley and Alan Pugsley, Shipyard started in Kennebunk as Federal Jack’s Brew Pub, They made their way to Portland in 1994 after they grew out of their space only a year later.

Maine’s oldest brewpub, Gritty McDuff’s, was founded in 1988 by Ed Stebbins and Richard Pfeffer, two friends who wanted to bring the feel and the beer of a true British pub to Portland. Gritty’s, as it’s known locally, makes traditional English ales (including “real ales” on cask) that pair great with their classic food selection.

Liquid Riot Bottling Company is the house that Novare Res Bier Cafe built, as that renowned Portland beer bar provided the impetus to open Liquid Riot right on the waterfront. Formerly known as In’finiti Fermentation and Distillation, this is one of the few combinations of restaurant, brewery, and distillery in one place. The space is striking, with floor-to-ceiling glass separating the three sections so customers can ogle the producers at work.

At the end of the tour, you can stay at our last stop or we will bring you back to Old Port Spirits and Cigars on Commercial Street where you can continue to explore the downtown area on foot!

Please note that tour stops may change without notice due to events and availability of staff at each venue.

Vegetarian hand pie from Union Kitchen, 1 Union Wharf, Portland

Available on-demand daily (except Saturday) with 2 departure times: 11 a.m. – 2 p.m. and 2:30 p.m. – 5:30 p.m.
Please arrive 15 minutes before tour start time for check-in and to ensure a timely departure.

  • Shipyard Brewing Company
  • Gritty McDuff’s
  • Liquid Riot Bottling Company

Walking Distance and Difficulty
1 mile to 1.5 miles of walking on brick and concrete sidewalks, with small inclines and limited stairs. There is also a short distance (200 yards) of walking on cobblestones.