Hit the Oxford County Cheese Trail

This is the bucket-list item for the long weekend. The Oxford County Cheese Trail is a self-guided tour with over 30 stops — spanning local cheesemakers, restaurants, farm stores, artisan boutiques, and museums — spread across Woodstock, Ingersoll, Tillsonburg, and the rural villages in between.

Tourism Oxford recommends picking a hub and planning about five stops in a day, since most locations are within 5–15 minutes of each other. For this weekend, don't miss Gunn's Hill Artisan Cheese near Woodstock, a standout producer of award-winning washed-rind and Dutch-style wheels, or the Golspie Dairy — a family-run farm since 1874 — where you can fill up on fresh milk and cheese curds from a one-of-a-kind farm vending machine.

Round out your trail day with a stop at Cheesy Cow Co. in Woodstock for the beloved Oxford Grilled Cheese Sandwich, a scoop at Dad's Ice Cream in Tillsonburg, and a pint at Upper Thames Brewing Company.

Explore Wildwood & Pittock Conservation Areas

Oxford County is blessed with two spectacular conservation areas that are tailor-made for a long weekend escape into nature. Wildwood Conservation Area near St. Marys boasts a 1,416-hectare outdoor playground with a 25-kilometre lake trail that's equally wonderful on foot or by bike. It's one of the finest cycling routes in the region and a gorgeous way to spend a May morning.

Pittock Conservation Area, just outside Woodstock, is perfect for families — with over 250 campsites and a reservoir ideal for paddling and fishing. If you haven't already booked a site, check availability; a spontaneous evening bonfire under a clear Southwestern Ontario sky is hard to beat.

Visit the Annandale National Historic Site

One of Oxford County's most striking landmarks, Annandale National Historic Site in Tillsonburg is a fully restored 1880s Victorian mansion built in the "Aesthetic Art Movement" style — constructed for Edwin Delevan Tillson, the town's first mayor. The ornate woodwork, stained glass, and hand-painted ceilings make it feel like stepping back into the Gilded Age.

While you're in Tillsonburg, wander through The Station Arts Centre, housed in a beautifully preserved 1879 train station. It features rotating gallery exhibits, a pottery studio, and a baggage room gift shop full of local artisan work — a wonderful place to find something unique to take home.

The Ingersoll Cheese Museum & Quilt Trail

Ingersoll is Ontario's premier cheese destination, and a visit to the Ingersoll Cheese and Agricultural Museum is a must — especially for families. With over 4,500 artifacts celebrating Oxford County's dairy heritage, a replica Mammoth Wheel of Cheese, and a delightfully cheesy outdoor playground, it keeps kids entertained while adults soak in the rich local history. Admission is pay-what-you-can, making it an easy addition to any itinerary.

While driving the countryside between towns, keep an eye out for the Oxford County Barn Quilt Trail — a series of large, vibrant quilt murals painted on the sides of barns and fences throughout the rural landscape. It's a uniquely beautiful, free experience that captures the county's artistic character perfectly.

Tee Off & Pick Fresh Berries

Oxford County offers some excellent golf to kick off the season. Innerkip Highlands Golf Club, Oxford Hills, and Sally Creek Golf Club are all welcoming long weekend rounds — and the spring conditions in this area are typically gorgeous by mid-May.

For something a little different, head to Berrylicious Fruit Farm to pick blueberries, elderberries, and raspberries with the family and enjoy one of their unique on-farm picnics. It's the kind of afternoon that embodies everything that makes life in Oxford County so good.

And don't overlook Jakeman's Maple Farm in nearby Sweaburg — maple cotton candy, maple coffee, maple popcorn — plus the scenic Trillium Trail right next door for a gentle post-snack stroll.