The Portland Regency
A 1895 former armory in the Old Port — 95 rooms, still family-owned, steps from the waterfront.
A 95-room hotel in Portland's Old Port, occupying an 1895 brick building that was originally the Maine state armory. Five floors of armory drill hall and barracks converted into hotel rooms, with the original interior brick and timber kept where it counted. The Regency has been family-owned for more than thirty-five years, which in a city now stuffed with Hilton flags makes it the obvious independent answer in walking-distance Portland.
Three blocks from the working waterfront, two from Commercial Street, one from the cobblestoned core. You can see why a state armory ended up here, and why the building was worth keeping.
The setting
Portland's Old Port is one of the better-preserved 19th-century commercial districts on the East Coast — granite-fronted brick buildings, cobblestone alleys, ferry slips at the foot of every street. The Regency takes up most of a block on Milk Street, between Exchange and Pearl. Portland Head Light is fifteen minutes by car at Cape Elizabeth; the Eastern Promenade trail starts ten minutes by foot. The Casco Bay islands ferry — Peaks, Chebeague, Long — leaves from the Casco Bay terminal four blocks east.
The drive from the Portland Jetport is fifteen minutes; Boston is two hours south.
The building
The 1895 armory has the proportions of its original purpose: thick brick exterior walls, deep window reveals, heavy timber framing inside. Public rooms include a high-ceilinged lobby with brass and velvet seating, the Twenty Milk Street restaurant, and a fireplaced library. The materials palette runs to brick, oak, brass, wool. The conversion preserved the drill-hall scale where it could and broke the rest into honest hotel-room floors.
The rooms
Ninety-five rooms across the armory and an attached small townhouse. Categories include standard kings and queens, junior suites, and a few larger executive suites with sitting areas. Rooms keep some of the original brick on a wall where the building allows; bathrooms are recently refreshed with tile and stone. From-rates open around $325, with significant variation by season — Portland's summer is genuinely peak.
Food & drink
Twenty Milk Street, the hotel's restaurant and bar, runs three meals. The menu leans New England — chowder, lobster roll, a steak — done well rather than reinvented. Non-guests can book and the bar is a frequent local stop. There is also a small breakfast room. For dinner outside the hotel, Fore Street, Eventide Oyster Co., and Drifters Wife are the longstanding picks within five minutes' walk.
On the property
The Regency Spa, on the lower level, is an old-school full-service spa — massage, facials, manicures, a sauna, and a small pool. There is a gym. There is no outdoor space beyond the front steps.
- Regency Spa with sauna and pool
- Twenty Milk Street restaurant and bar
- Fitness room
- Walking distance to ferries, restaurants, working waterfront
- Open year-round
Who it's for
- Travelers using Portland as a base for Casco Bay, the Maine coast, or the islands
- Couples doing a long weekend who'd rather walk to dinner than drive
- Family-owned-hotel partisans who'd rather not stay in another Hilton
- Architects and old-building people who'll appreciate the armory bones
Who it's not for
- Travelers needing a beach-resort program — for that, head to Ogunquit or Kennebunkport
- Anyone expecting modern minimalist design — this is a traditional historic property
- Pet owners (verify policy with the front desk)
Nearby
The Portland Museum of Art is five minutes' walk for Wyeth, Hopper, and the Winslow Homer studio (separate booking). The Eastern Promenade trail runs along Casco Bay from East End Beach. Portland Head Light at Fort Williams Park is fifteen minutes by car. For dinner: Fore Street remains the touchstone after thirty years; Eventide is the oyster lunch; Drifters Wife is the natural-wine picnic. The ferry to Peaks Island is a worthwhile day trip.
