Ask most people in the GTA what's in Collingwood and you'll get one answer, and it isn't Collingwood. It's the ski hill fifteen minutes west. Which is fine — Blue Mountain is genuinely great — but it means a lot of visitors drive right past a town that has spent the last decade quietly becoming the more interesting stop.
We're up here constantly, cameras in hand, shooting homes and businesses across South Georgian Bay. And the thing we've watched happen in Collingwood is a shift in identity: from the town near the resort to a place with its own harbour culture, its own food and drink scene, and a summer calendar that runs from late May straight through September.
So here are ten ways to spend a summer day in Collingwood that never require a chairlift.
01Paddle out of the harbour
Collingwood Harbour is the best beginner-friendly paddling water in the region — sheltered, shallow near shore, and calm most mornings before the afternoon wind comes up off Nottawasaga Bay. Rentals and lessons are easy to find in town, and stand-up paddleboards, kayaks, and canoes all work here.
The move for confident paddlers: point yourself toward the Nottawasaga Lighthouse and see it from the water, which is the only way it really makes sense. Go early. Check the forecast, wear the PFD, and don't underestimate an offshore breeze on an open bay.
02Take a sunset cruise past the lighthouse
If you'd rather someone else do the work, Collingwood Charters runs sightseeing and sunset cruises out of the harbour on a 65-foot tour boat. The standard trip is about an hour and a half — out past the Nottawasaga Lighthouse, into open Georgian Bay, then back as the sky goes to work behind you.
It is, without exaggeration, one of the best-value evenings in the region, and it books out on weekends. Reserve ahead, especially in July and August.
03Do the Craft Beverage Capital tour
This is the one that surprises visitors. Collingwood has leaned hard into a nickname it now mostly deserves: Ontario's Craft Beverage Capital. The self-guided trail links roughly a half-dozen local producers — Side Launch Brewing, The Collingwood Brewery, Black Bellows, Georgian Bay Spirit Co., Heretic Spirits, and Thornbury Craft just down the shore.
Georgian Bay Spirit Co. alone is worth the stop; it's one of the most awarded craft distilleries in the country and the reason half of Ontario's cottage docks have a can of gin smash on them. The town has real brewing and distilling history going back to the 1800s, so this isn't a marketing invention — it's a revival.
Obvious note: pick a driver, or book one of the local tour operators who runs the route for you.
Collingwood stopped being the town near the resort. It's a destination with its own gravity now — and summer is when that's most obvious.
04Catch a free concert at the Shipyards Amphitheatre
The Town's Live & Original summer series puts free live music on the waterfront at the Shipyards Amphitheatre (2 North Maple Street) on select summer evenings — original Canadian songwriters across folk, soul, alt-rock, and Celtic. Shows typically start early evening, and it's the rare event that works equally well for a couple on a date and a family with a four-year-old who needs room to run.
Bring a blanket and low chairs. Check the Town of Collingwood events calendar before you drive up, since the lineup and dates shift each season.
05Watch the sun go down at Sunset Point
The name isn't subtle and it doesn't need to be. Sunset Point Park is a west-facing stretch of pebble beach, picnic tables, playground, and open water where locals go for the last hour of light. Windsurfers and kiteboarders show up when the wind cooperates. Black Rock, just along the shore, is the swimming spot.
It's free, it's five minutes from downtown, and it's the single most reliable "oh, this is why people move here" moment we can point visitors to.
06Ride the Georgian Trail to Thornbury
The Georgian Trail runs about 34 kilometres along an old rail bed from Collingwood through Craigleith and Thornbury to Meaford — flat, crushed gravel, and shaded for long stretches. You don't have to do the whole thing. Ride to Thornbury, eat lunch, ride back, and you've had a genuinely great day on a hybrid bike with kids in tow.
Add to that the Collingwood Trails Network, roughly 60 kilometres of connected paths threading the town itself, and you can spend an entire weekend here without getting in the car again after you park.
07Spend a morning downtown on Hurontario Street
Collingwood's main street is one of the best-preserved heritage streetscapes in Ontario, and it's a real downtown — independent shops, cafés, bookstores, patios, and the restored Gayety Theatre anchoring it. The Collingwood Museum sits by the harbour and does a genuinely good job on the town's shipbuilding history.
Give it two unhurried hours on a Saturday morning. It's the part of a visit that most often turns into "what do houses cost here?"
08Hit the Saturday farmers' market
The Collingwood Downtown Farmers' Market runs through the warm months with local produce, baked goods, cheese, and makers. It's small enough to be pleasant and big enough to be worth the trip, and it pairs perfectly with item seven — market first, coffee second, main street after.
09Get above it all on the escarpment
You can hike the escarpment without setting foot on resort property. Pretty River Valley Provincial Park and the Nottawasaga Lookout conservation lands are both a short drive from town and deliver the postcard view — bay, farmland, and the long blue smudge of the shoreline — from a trail that costs nothing.
These are natural-environment areas, not manicured parks: proper shoes, water, bug spray, and a downloaded map before you lose signal.
10Time your visit to a festival
Collingwood's summer calendar has depth. The Festival for Canada takes over the waterfront around Canada Day with fireworks off Millennium Point — Harbourview Park and the promenade are the good viewing spots. The Collingwood Music Festival brings serious classical and jazz programming in August. And in 2026, the Collingwood Elvis Festival returned after retiring in 2019, running the last weekend of July and filling the downtown the way it used to.
Check dates before you book accommodation, in both directions: some people plan the trip around a festival, and some very reasonably plan around avoiding one.
Why we keep writing about this town
We photograph properties across Simcoe County and South Georgian Bay, which means we see the before-and-after of people's decisions. And the pattern in Collingwood is consistent: families come up for a weekend, do about four things on this list, and start doing math in the car on the way home.
That's not an accident. A town with a working harbour, a walkable main street, 60 kilometres of trails, and a legitimate food-and-drink identity is a town that holds up in every season — not just the twelve weeks with snow on the hill. The summer version of Collingwood is the one that convinces people, and it's the one most visitors never actually see.
Come up for a weekend. Bring the paddleboard. Book the sunset cruise. And when the math starts happening in the car on the way home, you'll at least know what you're buying into.
Event dates, hours, and operators change from season to season. Confirm details with the Town of Collingwood and the individual businesses before you plan your trip around them.