Cherry Tree Distillery

Cherry Tree Distillery pours from a Speakeasy-style tasting room on the ground floor of the Charles Vaughan house, a Late Victorian residence built in 1898, in the years after the fire that levelled much of downtown Windsor. The building spent early life as the Windsor House boarding house and has served several purposes since; today its parlours house a micro-distillery that keeps production deliberately small - gins, vodkas, rums and specialty liqueurs in micro batches, with house-made cordials and simple syrups completing a line-up that leans hard into the cocktail age: amaro, vermouth, coffee liqueur, hibiscus gin. Windsor sits on the Avon River at the gateway to the Annapolis Valley, roughly an hour from Halifax, which makes the distillery an easy first or last stop on a Valley loop. For the full distillery experience, Glenora, the province's oldest single malt whisky distillery, is a scenic drive further on near Mabou on Cape Breton Island.

A Tasting Room That Plays the Part

The Speakeasy conceit is more than paint - the room is staged around the Temperance era that once made private drinking a Nova Scotia parlour sport, and the hosts work the theme. Visitors sample spirits neat or as mini-cocktails, and the team will walk you through how to build the drinks properly at home. The reviews consistently single out the people: "top class entertainment by Jo and Dave," writes Sreejata Chatterjee, a Google Local Guide, who adds that "their hibiscus gin and coffee liq are amazing but the vermouth is to die for." Mark Botham, another Local Guide, dropped in during Windsor's Garlic Festival and found a "wonderful tasting room and friendly, knowledgeable hosts." Kevin Symes, also a Local Guide, echoes both points: "Great atmosphere with great local spirits" - he and his group worked through flights of cocktail samples alongside the amber rum, coffee liqueur and gins. With 14 Google reviews at a 4.8 average, the score is built on a small base, but the pattern is uniform: hospitality first, product second, theme throughout.

• Micro-batch spirits: several gins, vodkas and rums plus amaro, vermouth and coffee liqueur, all produced on site in small runs.
• Guided tasting flights: samples served neat or built into mini cocktails, with mixing instruction if you have the time.
• A themed room in a genuine 1898 building: the Charles Vaughan house survived the era of forced Temperance it now celebrates.
• Festival-friendly location: steps from Windsor's downtown events - the Garlic Festival crowd is a recurring source of walk-ins.

Pairing Windsor: Gerrish Street and the Blockhouse

A visit here is best treated as one stop on a downtown Windsor wander rather than a destination in its own right. The distillery sits at 163 Gerrish Street; five minutes' walk north, Fort Edward National Historic Site preserves one of the oldest blockhouses in Canada, a 1750 structure that watched over the Acadian deportation departures from Windsor - the heaviest history in the province sharing a block with gin flights, and a stop worth pairing before you head out on the Valley drive. Back down Gerrish Street, the Windsor Makers Studio & Art Market fills the old merchants' block with work from 300-400+ Nova Scotia artisans, and the Wild Nest Market keeps a curated vintage-and-maker space a few doors along. The Spitfire Arms Alehouse - "The Pub" to locals - is the obvious dinner pairing when the tasting room closes at eight. Between June and October, the Windsor & Hantsport area also hosts the Nova Scotia Pumpkin Festival events around the giant pumpkin weigh-off that gives Windsor its oddball claim to fame: this is the self-proclaimed World Pumpkin Capital, and the distillery's coffee liqueur has found its way into more than one autumn cocktail special in town. None of this is accidental - Cherry Tree deliberately positioned itself as the drink stop of a walkable downtown that punches well above its weight for a town of 3,600.

The Realities: Small Batch, Limited Hours

This is a two-person-scale operation, not a factory tour. Production is deliberately tiny, the tasting room keeps short, seasonal hours, and the experience depends on the hosts being behind the bar - visit at opening on a quiet Thursday and you may have the place to yourselves; arrive in the middle of a festival Saturday and expect to wait for stools. Summer 2026 hours were Thursday and Friday 4-8 pm, Saturday 12-8 pm, Sunday 11:30 am-3 pm, with off-season schedules posted on the distillery's own site - check before driving out, because winter hours are trimmed further. The distillery does not maintain a listed phone line; the website and Facebook page are the reliable channels for hours, restocks and event nights. Cards (Visa, MasterCard, Amex, Discover) are accepted. There is no food service, so pair a visit with downtown Windsor - the Spitfire Arms Alehouse and the shops of Gerrish Street are within a few minutes' walk, and the Fort Edward blockhouse is a five-minute stroll up the street. One more expectation to set: because everything is micro-batch, the shelf changes - the vermouth a reviewer raved about may be sold out, and the replacement may be something you have never heard of. That is the deal with small producers, and the hosts treat it as a feature.

Windsor's craft-drink identity runs wider than one distillery, and Cherry Tree is the newest proof of the pattern. The province's larger producers - Glenora in Cape Breton, Ironworks in Lunenburg, Coldstream Clear up the Northumberland Shore - built the category; the micro-distillery wave that followed concentrates in small towns where a single historic building can carry a brand. The Charles Vaughan house does that for Windsor: the 1898 build gives the distillery its Speakeasy story, its parlour-scale rooms, and its reason to be walkable downtown rather than out on a highway strip. For visitors building a Valley drinks itinerary, the practical sequence is Windsor first (Cherry Tree plus the Spitfire Arms for a pint), then west along Highway 101 into the Annapolis Valley winery belt - the same corridor that carries Lightfoot & Wolfville, Luckett, and the Grand Pré estate wineries. Plan the driving, not the tasting: the Valley's distances look short on a map and add up quickly on the ground.

The Practical Details: Location, Hours & Essentials

Address & Location
163 Gerrish Street, Windsor, NS B0N 2T0 - in the downtown core, on the same street as most of Windsor's shops and restaurants, about an hour's drive from Halifax via Highway 101 (Exit 6).

Hours of Operation
Summer hours (as posted for 2026): Thursday-Friday 4-8 pm, Saturday 12-8 pm, Sunday 11:30 am-3 pm. Closed Monday-Wednesday. Off-season hours are reduced - verify current times on cherrytreedistillery.ca before visiting.

Price Range
Tasting flights and mini-cocktail samples run in the $10-20 range; bottles typically $30-60 for micro-batch spirits and liqueurs.

Reservations
None required for regular tastings. Groups and private events should contact the distillery in advance through the website or Facebook page.

Parking
Street parking on Gerrish Street and adjacent downtown blocks; free.

The short version: for anyone touring the Annapolis Valley's drink scene, Cherry Tree is the Windsor stop - a genuine 19th-century building, a Speakeasy room with personality, and a small, inventive line-up that owners Jo and Dave will happily talk you through cocktail by cocktail.