May Events Across Lake Country & Beyond
May is when cottage country wakes up. The long weekend kicks off the season, the docks go in, the boats come out of storage, and the region comes alive after a long winter. It's one of the best months to be anywhere across the five regions we call home — and there's plenty happening to make the most of it.
May 16–18 · Across All Five Regions
Victoria Day Long Weekend — Cottage Season Officially Begins
The May long weekend is the unofficial start of cottage season across Simcoe County, Muskoka, Parry Sound, Kawartha Lakes, and Haliburton. Docks go in, boats get launched, and the lakes fill up for the first time all year. Whether you're heading to your own place or exploring the region for the first time, there's no better weekend to be in cottage country than this one.
May 23 · Muskoka Brewery, Bracebridge
Pups & Pints at Muskoka Brewery
Stop by the Muskoka Brewery Taproom from 12–5pm for an afternoon of craft beer, dog-friendly treats, great food from The Creative Plate, games, and live entertainment. Dogs are not just welcome — they're the guests of honour. This free community event supports the Ontario SPCA and Humane Society, with donations of pet supplies collected at the Taproom. A perfect post-dock-installation afternoon for the whole family — four-legged members included.
May 23 · Stanhope Municipal Airport, Algonquin Highlands
Fly-In to Spring — Classic Cars, Aircraft & Live Music
Running 10am to 3pm and free to attend, this is one of the most unique events in the Haliburton Highlands. Classic cars and antique aircraft on display, food trucks, live music, artists and artisans, and face-painting for the kids. Whether you're a car enthusiast, an aviation buff, or just looking for a great family outing, the Fly-In to Spring is the kind of only-in-cottage-country event you'll be telling people about after.
May 24 · Bracebridge Fairgrounds, Muskoka
Muskoka Spring Holistic Healing Fair
The Muskoka Spring Holistic Healing Fair returns to the Bracebridge Fairgrounds, bringing together wellness practitioners, artisans, and holistic health vendors under one roof. A great way to round out the long weekend with something a little different — and a reminder that Muskoka is as much about slowing down and recharging as it is about the water.
May Long Weekend Onward · Haliburton Highlands
Haliburton Art Studios & Galleries Open for the Season
Starting May long weekend, art studios and galleries across the Haliburton Highlands open their doors for the season — three locations with work running right through Thanksgiving. Whether you're a longtime collector or just love discovering local talent, exploring the Highlands gallery scene is one of the great cottage country traditions. Watch for signage as you drive the back roads and don't be afraid to stop in.
May is a big month across all five regions. If you're thinking about spending more time up here — whether as a visitor, a buyer, or someone already in the market — I'd love to show you around. There's no better way to understand what cottage country living actually feels like than being here when the season starts.
📞 705-242-5764 | bill@lcre.team | Book a call →
Lake Country Real Estate Team | eXp Realty | Serving Simcoe County, Muskoka, Parry Sound, Kawartha Lakes & Haliburton
