What To Do This Weekend in Port Perry: October 2 to 4, 2026

Friday, October 2: the pumpkin hunt begins, and a relaxed night out

The weekend’s family anchor starts Friday. The Port Perry BIA’s I Spy the Pumpkin hunt runs October 2 to 4 across the Queen Street core: pick up a free Pumpkin Passport at a participating shop or at the BIA table in front of Brock’s at 168 Queen Street, then visit the businesses and spot the pumpkin hidden in each window. Each pumpkin carries a fall-themed word to record on the passport, and completed passports go into the draw for prizes. The BIA’s I Spy the Pumpkin page lists the participating stores and prize details, and hours vary by shop, so check it before you head out.

Friday night is a low-key one. The Port Perry Legion at 484 Bay Street runs its drop-in line dancing class from 6 to 8 p.m., no registration needed, a friendly way to close the work week. Dinner stays on Queen Street: Marwan’s Global Bistro at 187 Queen Street, Saffron Eatery for a quick, flavourful meal, or the Piano Cafe and George Stanley Inn at 217 Queen Street for a calmer seat inside a restored 1884 landmark. Old Flame Brewing Co. at 135 Perry Street runs its Friday pop-up kitchen with live music in the taproom; see the brewery’s experiences page for the night’s lineup.

Saturday, October 3: market morning, pumpkins and patio music

Saturday starts at the water. The Port Perry Lakefront Farmers’ Market runs 8 a.m. to 3 p.m. on Water Street at the foot of Queen Street, beside Palmer Park on Lake Scugog. The 2026 season ends October 10, so this is one of the last full harvest Saturdays: seasonal produce, baking, meats, cheese and handcrafts, with the grain elevator rising behind the stalls. The market’s official site posts each week’s vendors.

Then the pumpkins. Pumpkin Palooza at Willowtree Farm, 975 Durham Regional Road 21, runs Saturday and Sunday from 9:30 a.m. to 4 p.m., with last entry at 3 p.m. Tickets are $12 online and $15 on-site for ages 2 and up, and cover the wagon ride to the pumpkin patch, the straw jump, mini pumpkin games, the mini corn maze and family games. Book ahead on the farm’s Pumpkin Palooza page.

Back in town, the afternoon splits between Queen Street and the lake. Port Perry’s Vintage Market at 1894 Scugog Street is open 10 a.m. to 5 p.m., Meta4 Contemporary Craft Gallery sits mid-block at 200 Queen Street, and the I Spy the Pumpkin hunt keeps kids busy in the shop windows. Old Flame Brewing Co. hosts Saturday afternoon live music from 1 to 5 p.m. at 135 Perry Street, pouring traditional German-style lagers inside the 1874 Ontario Carriage Works building.

Queen Street handles dinner, and the taproom at Old Flame stays open for an evening pint. If the night is crisp, the 5 km Waterfront Trail System along Lake Scugog is a short walk from downtown for a post-dinner stroll under the lights.

Sunday, October 4: farm music, the hunt’s last day, and a lakeside close

Sunday belongs to Willowtree Farm. Live Music Sundays run noon to 3 p.m. on the patio, with local musicians and the farm cafe serving food and drinks alongside, and Pumpkin Palooza runs again from 9:30 a.m. to 4 p.m., so the farm makes an easy full morning. The Live Music Sundays page has the day’s lineup.

In town, Sunday is the last day of the I Spy the Pumpkin hunt, and the national Culture Days festival closes October 4. Scugog Arts has been the local organizer behind the township’s free arts events this fall; check the Scugog Arts Culture Days page before the weekend for anything still running.

If the weather holds, save an hour for the water. Palmer Park, Kinsman Beach and the 5 km Waterfront Trail System along Lake Scugog are all a short walk from downtown, with the 1873 grain elevator and open water at the end of Queen Street.