After watching a performance of the Shaw Festival’s “Brigadoon,” the streets of this magical town on Lake Ontario might seem like a real-life version of the Scottish village depicted in the Lerner and Loewe musical. On a recent evening, the place felt frozen in time, with horse-drawn carriages rolling down a main street lined with Victorian buildings and flower beds. But the Irish playwright and political activist Bernard Shaw, the 1925 winner of the Nobel Prize for Literature, would be proud of the modern discussions and debates that his dramas, comedies and historical plays still generate over wine from the local vineyards. Only 45 minutes from Buffalo, Niagara-on-the-Lake is also a mere 20 minutes from the Canadian side of Niagara Falls, and beyond its rich theatrical offerings, the town is filled with enough diversions — whether culinary, cultural or outdoorsy — to easily fill a weekend.
1) 3 p.m. An afternoon stroll
Get the lay of the land by strolling down Queen Street, filled with clothing, cookery, fudge and wine shops. Anglophiles will be happy to find a number of stores selling British products, from tea towels and totes to blankets and biscuits. Visit Greaves Jams & Marmalades and take advantage of Niagara’s fruit belt by picking up a peach chutney, apple jelly or boysenberry jam (6.25 Canadian dollars a jar, or about $4.80). The Edward Spera Gallery displays the artist’s paintings and drawings of animals — from tigers in Nepal to great white sharks in South Africa. After checking out the Beau Chapeau, which stocks every imaginable hat, from derbies and fedoras to Panamas and berets, duck into the Niagara Apothecary museum, a restored 1869 pharmacy with original interior fittings and cure-alls for everything from hair loss to tuberculosis.
2) 5 p.m. Certifiably good
Steps from the three Shaw Festival theater venues is the perfect place for a hearty pre-dinner snack. Pie’za Pizzaria, is a restaurant certified by the Associazione Verace Pizza Napoletana for making pizzas in the authentic Neapolitan tradition. Even the oven in this cozy spot comes from Naples. Try the Caprese salad, made with local fresh mozzarella, and a shareable 12-inch pizza like the La Spieza, billed as a “meat lover’s dream,” with a spreadable spicy salami. A meal for two, without wine is about 40 dollars.
3) 7 p.m. Shaw time
Though named after Shaw, who wrote more than 60 plays, the Shaw Festival, founded in 1962, pays homage to a variety of contemporary playwrights. With 10 or more productions each year (this year there are 13), it has grown into an international destination for theater-lovers with more than 250,000 attending each season. Running from the beginning of April through November, this season’s roster includes “Cyrano de Bergerac,” “The Horse and His Boy,” “Rope” (a thriller Alfred Hitchcock made famous on the silver screen) as well as “The Glass Menagerie,” and “A Christmas Carol” at the season’s close. One of this year’s two Shaw treats is “Man and Superman with Don Juan in Hell.” Performances take place at different times of the day in the Festival Theater, the Royal George Theater, and the Jackie Maxwell Studio Theater, making it possible to hit a handful of productions in a single weekend. Tickets range from 30 dollars for those under 30, to 135 dollars for an orchestra seat. Children under 18 pay 25 dollars.
4) 10 p.m. A Night cap
Stop in at the Churchill Lounge at the Prince of Wales Hotel for an after-dinner drink. Since Saturday’s agenda includes wine tasting, take a look instead at their lengthy list of whiskies. Though the décor in the hotel is over-the-top Victorian (Queen Elizabeth stayed here in 1973), the bar — with its bookshelves, leather chairs and wood-paneled walls — feels Old World elegant and stays open until 1 a.m. on Friday and Saturday nights, often featuring a pianist.
5) 9 a.m. A sweet start
Canada is known for its butter tart, a morsel of flaky crust surrounding a sweet filling. At the Niagara Home Bakery fill a bag with a variety of their plain, pecan, raisin and chocolate caramel butter tarts. Then head to Balzacs and pick up a café Canadien. The double shot of espresso with steamed milk includes maple syrup, with the micro foam on top shaped into a maple leaf. Take your coffee and tarts to a picnic table just steps away in Simcoe Park and watch the town wake up over breakfast.
6) 10 a.m. Zoom off
A short distance from town is Zoom Leisure Bikes, where you can pick up a bike (hybrid, easy comfort, tandem, power-assisted) or have it delivered for free. Rental rates start at 20 dollars for a half day and 30 dollars for a full day. Tour packages include tastings at four local wineries and one brewery. But first head off to the Niagara River Recreation Trail, a bicycle path (56 kilometers, or about 35 miles) that runs alongside the Niagara River and passes many historic sites, including Fort George, the main headquarters for the British Army during the War of 1812, where the Canadians fought off several American invasions.
7) 1 p.m. Winery respites
Whether riding on a bike, hopping on and off the Wine Trolley, or jumping into a van with the Winery Guys Tours, tasting the local wines at dozens of nearby wineries is a must — as is lunch. If the weather is nice, stop at the Barrel House Grill at Peller Estates Winery, a casual first-come-first-served outdoor restaurant with a variety of burgers: ribeye, chicken, portobello mushroom and brisket. Pair it with a Daiquirosé — a rum, rosé, lime juice cocktail — and enjoy the view of the vineyard. An indoor option (with an outdoor patio) is Two Sisters Vineyard, where Kitchen 76 serves an Italian-inspired menu. Share a bottle of sauvignon blanc and small plates like crispy artichokes or Sicilian rice balls. Lunch for two with wine at both places is around 70 dollars.
Make time for Wayne Gretzky Estates, a tribute to the former Canadian professional ice hockey player and head coach who played in the National Hockey League. For 35 dollars, you can take a behind-the-scenes tour of the facility, complete with a photo gallery of Mr. Gretzky’s career and a shop selling hockey pucks, T-shirts and other souvenirs emblazoned with the number 99 (his retired jersey number). Sidle up to the whisky bar, or head to the beer garden (which becomes an ice-skating rink in the winter) and try his signature No. 99 Rye Lager, or, if you have drunk enough, their homemade kombucha.
8) 3 p.m. Fairways and facials
There are many reasons to visit the Niagara-on-the-Lake Golf Club, situated right in town. Established in 1875, it is not only North America’s oldest golf club, but the entire nine-hole course set on the shores of Lake Ontario is also open to the public. If you are not a golfer, there is a patio bar and restaurant with perhaps the best view in town of the lake. With peaches so plentiful in this region, sip on a peach mojito or frozen peach bellini and watch the boats go by. Or head to the 100 Fountain Spa, with outdoor hot springs, an indoor saltwater pool and heated outdoor pool. Try a Vino facial, an 80-minute grape extract exfoliation for $160.
9) 7 p.m. Tasting treat
If not headed to the theater, there is another theatrical experience to enjoy via the tasting menu at the Trius Winery, one of the oldest wineries in the area. The five-course, 95-dollar-menu (with wine pairings add another 50 dollars), includes Ontario delicacies: mushroom soup with truffle goat cheese, pickled grapes and ice-wine beets, roasted rib-eye, pulled short ribs with ice-wine onion jam, and a rhubarb and strawberry trifle. Watch the sun go down beyond rows of grape vines while you enjoy the fruits of Trius’s labor.
10) 10 p.m. Music past midnight
The Olde Angel Inn, a British-style pub, was established in 1789 and rebuilt in 1815 after the War of 1812. Not only does it harbor a ghost (a Canadian captain on the verge of joining the British troops, then killed at the inn by an American soldier), it also has local bands performing until 12:30 a.m. Friday and Saturday nights. Toast the ghost, and the British flag that flies above the inn (to keep the ghost at bay), with a 12-year-old Glenfiddich.
11) 9 a.m. Your meal for the day
One cannot visit Canada without trying Poutine, a native dish of home fries topped with cheese curds and gravy. Eat breakfast at the Sunset Grill (62 Queen Street), where they serve it as a morning meal with the added ingredients of Peameal-style bacon, sautéed onions, and Cheddar cheese topped with Hollandaise sauce for 9.99 dollars.
12) 11 a.m. Jet off
Though closed this summer, because of the high water level affecting the dock, the Whirlpool Jet Boat Tour facility in Niagara-on-the-Lake should be open next year (this season customers are being sent to their other outlet at Niagara Falls). Don’t miss the chance to ride on their custom-built vessels that navigate the strong rapids on the lower Niagara River, a seven-mile gorge carved out by the strong currents in the Niagara River. With hundreds of thousands of gallons of water flowing over the falls every minute, it is a journey like no other. Get wet on this wild ride to acclimate back to reality after the quiet of Niagara-on-the-Lake. Cost: 69.95 dollars for an adult and 44.95 dollars for children, who must be at least 40 inches tall
Airbnb accommodations are abundant in Niagara-on-the-Lake, with one-bedrooms and suites often available for under 100 dollars a night, but so are Bed and Breakfasts, such as St. Andrews House B&B, (double rooms under 200 dollars), where the Scottish owners serve a hot breakfast each morning, complete with muffins and croissants.
While Vintage Hotels runs the four largest luxury hotels in town, The Oban Inn is an intimate 26-room boutique hotel right on the lake that has a spa, dining room and outdoor swimming pool. The average nightly rate runs around 300 dollars, depending on the time of year.
52 PLACES AND MUCH, MUCH MORE Follow our 52 Places traveler, Sebastian Modak, on Instagram as he travels the world, and discover more Travel coverage by following us on Twitter and Facebook. And sign up for our Travel Dispatch newsletter: Each week you’ll receive tips on traveling smarter, stories on hot destinations and access to photos from all over the world.