Since it first threw open its Tudor-style doors in 1878, Windsor's oldest tavern has kept whistles wet and toes tapping with beers, live music, and a full menu of sandwiches and pub-style entrees such as fish 'n' chips and shepherd's pie. A dozen different brews flood from the tap, slaking the thirsts of guests plugging away at open mic and trivia nights. Beyond the main dining room’s checkered floors, long communal-style tables, and crimson walls, private rooms host parties of up to 100 merrymakers or several million thimbles.
Gilligan's serves up more than 20 varieties of gourmet hamburgers made fresh daily with local ingredients free of artificial preservatives and fillers. The grill's triple-A half-pound, hand-packed beef creations, derived entirely from local producers, include the vaunted fire-grilled original burger, adorned with the house grill sauce ($10+), as well as more exotic offerings such as the Los Cabos burger, which sports zesty salsa, guacamole, a dollop of sour cream, and a lace mantilla ($11+). Burgers fashioned from ground turkey ($10) and buffalo ($12) provide poultry and bison alternatives, and the dry-rub St. Louis side ribs can quell pork-centric cravings and coat palates and fingers in a tangy coat of barbecue sauce ($12/half rack, $18/full). Old-fashioned milkshakes in strawberry, vanilla, and chocolate varieties arrive topped with whipped cream, chocolate sauce, and a cherry and deliver moving arguments in favour of lactose tolerance ($5).
Hurricanes Pub and Grill welcomes patrons into a classic neighbourhood meeting den where with live sports broadcasts and trivia games accompany sandwiches, burgers, and social gatherings. An extensive menu proffers baskets of the pub's celebrated chicken wings ($10.60 for eight), bathed, like Victorian dandies, in a choice of spicy or sweetened sauces. Six-ounce lean beef Hurriburgers in breeds such as the barbecue and onion-topped hickory smokey ($7.75) and the peameal bacon–backed Great Canadian ($7.10) graze tables until patrons ensnare them in a bun and match them with a side of fries ($1.79). Hands take a breather as forks get to flaking pan-fried tilapia ($10.75) crusted in tortilla bits and accompanied by rice and steamed vegetables. Hurricanes Pub and Grill entertains its diners with free WiFi and Buzztime trivia as well as nine TVs bathing tables in the light of sports fireworks. Guests dine at rustic wood tables on two split levels, ensconced in exposed brick walls lined with vintage signs, sports banners, and needlepoint Monets.
The Pour House Pub, an upscale gastropub, serves a menu full of foodie-pleasing pub favourites alongside draft beers, local wines, cocktails, and Scotches. Like a monocle-wearing robot, dinner melds classic fare with a modern touch, as evidenced by the goat-cheese topped gourmet potato skins ($7.95), sturdy steak sandwich ($9.95), and radiant veggie panini ($7.95). The slab of ribs ($9.95 for half, $17.95 for full) leads the hearty entree parade, and a panoply of pastas ($10.95–13.95) bring up the rear in grand Apennine style. The pub’s nimble-fingered tapsters ensure a phrenologically sound head on a pint of Labatt Blue, Stella Artois, Sapporo, and other draughts, and fanciful cocktails, such as a Professor Plum or a Red Lotus (both $6.95) illustrate their alchemic abilities. Exposed brick walls, ductwork, and Tudor-esque wooden beams conspire with stained glass accents and low lighting to keep diners as cozy in their seats as dinner is cozy in their stomachs.
Martinis and conversation reign at Vermouth, a place that enshrouds imbibers in 1920s-style environs. Friends and clandestine groups of treasure hunters can peruse a menu of creative cocktails and shareable appetizers such as shrimp cocktails and spreadable artichoke dip. Barkeeps blend fresh fruit into seasonal specialty martinis including the raspberry currant, and mixologists shake classic vodka and gin recipes. Foursomes may alternatively toast the completion of their Monopoly game by pouring from a shared pitcher of sangria. The establishment's interior mixes vintage and contemporary decor, inviting patrons to linger near the fireplace or lounge on plush couches.
To craft their signature paninis, Bar Domani’s chefs layer freshly baked focaccia bread with cuts of chicken, veal, and fresh vegetables, topping everything off with fine cheeses. Outside the kitchen, guests raise glasses of specialty martinis over plates of tiramisu in the intimate dining room.