Parry Sound wraps around a deep harbour on the eastern shore of Georgian Bay, with a long rail trestle striding over the town and pink granite along the water. Once the summer boats are tucked away, the town gets quieter and cozier, and its stage, hockey shrine and hilltop lookout become the heart of a good outing. Every idea below draws on what local venues and the Town have published for the late fall and winter of 2026.

Nights at the Stockey Centre

Stockey Centre Shows: The performing arts centre at 2 Bay Street sits right on the harbour, and its late fall lineup is full of music. Classic Troubadours, a five piece Canadian band, plays the songs of James Taylor, Joni Mitchell, Jackson Browne and Carole King on Friday, November 20 at 7:30 p.m. Cape Breton's Men of the Deeps bring their December Coal program on December 2, and The Forever Highwaymen tribute to Waylon, Willie, Johnny and Kris rolls in on December 4. On December 9 a jazz trio performs the 1965 soundtrack of A Charlie Brown Christmas, and on December 17 the screen shows the film White Christmas. Pick the show that matches the music you both grew up with.
Sleigh Bells and Brass: For a daytime date, the Orillia Silver Band plays its traditional holiday brass concert on Sunday, November 29 at 2 p.m. Tickets come from the Stockey box office.
Winter Concerts: Looking past the holidays, two time JUNO winner William Prince plays an acoustic evening on January 19, 2027, and Matt Andersen, whose latest album mixes tender folk with stirring soul, visits on February 13, 2027. Either one makes a thoughtful gift for a partner who loves live music.

The Canadian Pacific Railway trestle crossing treetops and homes in Parry Sound, seen from the Tower Hill Lookout.

Hockey and Local History

Bobby Orr Hall of Fame: Parry Sound is the hometown of Bobby Orr, and the hall honouring him shares the Bay Street building with the Stockey Centre. Through the winter it opens Wednesday to Saturday from 10 a.m. to 5 p.m. Spend the afternoon reliving great hockey moments, then pair your visit with an evening show next door.
Museum on Tower Hill: The West Parry Sound District Museum at 17 George Street invites you into the stories of the local community. Winter hours run Wednesday to Saturday from 11 a.m. to 4 p.m., and it sits just steps from the lookout tower, so the two fit easily into one afternoon.

Views Over the Harbour

Tower Hill Lookout: Climb the 130 steps of the 30 metre observation tower for a 360 degree view of the harbour and Georgian Bay. From the top you can watch boats and float planes below and trace the famous Canadian Pacific Railway trestle across town. The Heritage Garden at the base is planted and cared for by volunteers.
Waterfront Fitness Trail: The Rotary and Algonquin Regiment Fitness Trail follows the shore for 6 km on a pink granite path, with interpretive plaques about the community along the way. Walk it hand in hand at dusk and try a fitness station or two if you are feeling playful.

Parry Sound harbour and town rooftops seen from the tower atop Tower Hill.

Holiday Lights and the Parade

Light Up The Park: On Friday, November 20 at 6 p.m., Market Square Park switches on its Christmas lights to start the season. Arrive early, then walk down to the Stockey for the 7:30 concert that same night.
Santa Claus Parade: This year's parade theme is Santa's Workshop, and the floats roll through town on Saturday, November 28 at 4 p.m. If severe weather cancels it, the Town has set Tuesday, December 1 at 4:30 p.m. as the backup date.
Christmas Artisan Show: The fourteenth annual artisan show fills the Stockey Centre on Friday, November 27 from 2 to 7 p.m. and Saturday, November 28 from 10 a.m. to 3 p.m. Entry is by donation. Set a small budget and pick out a handmade gift for each other.

On the Ice

Saturday Public Skating: The Bobby Orr Community Centre offers free public skating on select Saturdays from noon to 12:50 p.m., including November 14, 21 and 28 and December 12 and 19. Sessions can be cancelled for tournaments, so check the Town page first. Skate in the hometown of hockey's most famous defenceman, then warm up over lunch downtown.

Sunset over the water of Parry Sound seen from the waterfront fitness trail.

Sample Date Itineraries

1. Lights and Troubadours (Nov 20): Light Up The Park → dinner downtown → Classic Troubadours at the Stockey Centre

2. Hilltop Afternoon: Museum on Tower Hill → climb Tower Hill Lookout → sunset walk on the fitness trail

3. Parade Weekend (Nov 27 to 28): Christmas Artisan Show → lunch in town → Santa Claus Parade at 4 p.m.

4. Hockey Saturday: Free public skate at noon → Bobby Orr Hall of Fame → an evening show at the Stockey

Pro Tips for Memorable Dates

From November 1 to April 15, the Town does not allow parking on its roads or in Town lots between 3 and 7 a.m.
The Hall of Fame and the Stockey Centre share one building, so plan a daytime visit before an evening concert.
The Museum on Tower Hill closes Sunday through Tuesday in winter.
Buy Stockey film tickets in advance, as the venue encourages.
Bring warm gloves for the open air lookout tower.

Between the harbour views, a hall full of hockey history and a lively winter stage, Parry Sound gives couples plenty of reasons to slow down together this season.

Last reviewed: October 2026

Photo credits: The CPR trestle from Tower Hill by СССР, CC BY-SA 2.5 ca, via Wikimedia Commons; Parry Sound harbour by WabbitWanderer, CC BY-SA 2.0, via Wikimedia Commons; Sunset from the fitness trail by WabbitWanderer, CC BY-SA 2.0, via Wikimedia Commons.