Ten unmissable cultural road trips within two hours of Toronto

The Camping Trip

WAYHOME

Burl’s Creek Event Grounds, Oro-Medonte. July 22 to 24. Diehard music fans pitch tents at this summer carnival, which features outdoor art installations and sets from Arcade Fire and the Killers. A $600 VIP package buys coddled urbanites raised and shaded seating, custom cocktails, access to late-night parties, and, for the sore and stinky, luxe massages and shower services. PIT STOP: Dickey Bee Honey in Innisfil for apiary tours and wildflower honey.

The Drama Destination

STRATFORD FESTIVAL

Stratford. To Oct. 30. The Bard bonanza goes meta this year with the North American premiere of Shakespeare in Love, a stage adaptation of Tom Stoppard’s sweet and salty costume drama. Also worth checking out: the Stratford Summer Music Festival, which features outdoor sunrise concerts and music on a barge. PIT STOP: The Berlin, a new farm-to-table spot in Kitchener from ex–Langdon Hall super-chef Jonathan Gushue.

The Bucolic Concert Hall

WESTBEN BARN

6698 County Rd. 30 N., Campbellford. July 1 to 31. The stunningly rustic timber-frame barn was designed with acoustics in mind. This summer, it hosts the premiere of The Pencil Salesman, a whimsical chamber opera starring Met baritone John Fanning. PIT STOP: The Mary Poppins–esque antique carousel in Roseneath, which holds 40 basswood horses and dates back to 1906.

The Hootenanny

HAVELOCK JAMBOREE

10 Country Rd. 48, Havelock. Aug. 18 to 21. The annual hoedown is more Deep South than southern Ontario. RVs, steel-toed boots and line dancing prevail, along with performances from sibling trio the Band Perry and American Idol superstar Scotty McCreery. PIT STOP: Oshawa’s Hollywood Cone for a Mutant Milkshake (they’re blended with Skor bars, pie slices, funnel cakes and other delicious monstrosities).

The Art Party

DRAKE DEVONSHIRE

24 Wharf St., Wellington. To Oct. 30. True to its Queen West roots, the quaint and quirky Prince Edward County hotel hosts an outdoor art extravaganza, featuring giant murals, interactive installations and playful steel sculptures scattered all over the grounds. PIT STOP: A romp through the fields at Prince Edward County Lavender. The on-site boutique sells luscious soaps and lotions.

The Boozy Film Festival

MOVIE NIGHT IN THE VINEYARD

1249 Niagara Stone Rd., Niagara-on-the-Lake. Various dates. The classiest movie theatre in Ontario is at Trius Winery, where guests chill on lawn chairs and sip rosé. The 2016 schedule includes Spectre for Bond fans and The Force Awakens for BB-8 groupies. PIT STOP: A dip in the swimming hole at DeCew Falls, a secluded Shangri-La with a 70-foot waterfall.

The Can-Rock Cathedral

JACKSON-TRIGGS AMPHITHEATRE

2145 Niagara Stone Rd., Niagara-on-the-Lake. June 9 to Sept. 9. At the winery’s glowing coliseum, showgoers drink pinot while taking in mellow sets. Among them: renaissance man Bahamas, troubadour Dan Mangan and indie faves Stars. PIT STOP: The Ice House Winery, which serves up wildly refreshing icewine slushies.

The Rural Revue

4TH LINE THEATRE

779 Zion Line, Millbroo. Aug. 2 to 27. This theatre troupe stages original Canadian dramas on a patch of farmland, using the barns and paddocks for scenery. The standout is The Bad Luck Bank Robbers, which recreates a real-life TD Bank heist from 1961. PIT STOP: Mercury Chocolates in Port Hope, which makes truffles in such fab flavours as pink peppercorn, key lime and cherry shiraz.

The Edwardian Spectacle

SHAW FESTIVAL

Niagara-on-the-Lake. To Oct. 23. This year, the picturesque theatre fest breaks away from George Bernard Shaw’s prim comedies of manners with a production of Stephen Sondheim’s gruesome gorefest Sweeney Todd and a trippy new take on Alice in Wonderland.
PIT STOP: The Kowalik family’s roadside market for bushels of just-picked cherries, apricots and peaches.

The Barn Bash

HAYLOFT DANCEHALL

344 Salmon St., Picton. Various dates. Last year, the owners of the Dakota Tavern on Ossington transformed an abandoned barn in Picton into a fairy-lit country fantasy with craft beer and live music. On the roster this summer: shows from indie stalwarts the Sadies, Yukon Blonde and Mounties. PIT STOP: Dead People’s Stuff, a weird and wonderful antique shop in Bloomfield stocked with kitschy Canadiana.