End-of-Summer Ontario Road Trips You Can Still Take

As the summer season begins to wind down, there’s still plenty of time for a last-minute road trip adventure in Ontario! Whether you’re looking to explore charming small towns, breathtaking natural landscapes, or relaxing cottage country vibes, Ontario has endless options to end your summer on a high note. Here are four road trips you can still squeeze in before the cooler weather arrives.

1. Prince Edward County: Wineries, Beaches, and Art

Why Go: Prince Edward County is a top destination for anyone looking to enjoy a blend of laid-back charm, stunning scenery, and vibrant local culture. Late August is the perfect time to visit, as the region’s wineries are in full swing, and the beaches are still warm enough for a dip.

Highlights:

• Wineries and Breweries: Sip your way through local wineries like Sandbanks Winery and Hinterland Wine Company.

• Art and Culture: Explore the vibrant arts scene in Picton and Bloomfield, where galleries and artisan shops offer unique finds.

• Beaches: Relax at Sandbanks Provincial Park, home to some of the best sandy beaches in Ontario.

Tip: Visit during the week to avoid weekend crowds and enjoy more intimate tastings at the wineries.

2. Tobermory & Bruce Peninsula: Crystal Clear Waters and Rugged Beauty

Why Go: Tobermory is an outdoor lover’s paradise. The turquoise waters of Georgian Bay, rugged limestone cliffs, and unique rock formations make it one of Ontario’s most stunning destinations. It’s the ideal spot for those looking to mix adventure with breathtaking scenery.

Highlights:

• The Grotto: Hike to this famous sea cave with crystal-clear waters—perfect for a refreshing swim.

• Flowerpot Island: Take a boat tour to this iconic island and explore its unique rock formations and hiking trails.

• Scenic Hikes: Walk along the Bruce Trail for panoramic views of the bay and explore Bruce Peninsula National Park.

Tip: Book your park entrance and boat tour tickets in advance, as these tend to sell out quickly, especially in late summer.

3. Thousand Islands: Cruises, Castles, and History

Why Go: Nestled along the St. Lawrence River, the Thousand Islands region is a picturesque getaway filled with history, adventure, and beautiful riverfront views. Late summer is the perfect time to cruise through the islands and explore quaint villages along the water.

Highlights:

• Boat Cruises: Take a scenic boat cruise to see the famous Boldt Castle and the endless archipelago of islands.

• Cycling and Kayaking: Rent a bike or kayak to explore the islands up close, including waterfront trails and secluded bays.

• Historic Sites: Visit the quaint village of Gananoque and tour historic sites like Fort Henry.

Tip: Combine your road trip with a stay at a waterfront inn or bed-and-breakfast for a relaxing end to your summer escape.

BONUS: Read my honest review of the 1000 islands cruise I took from Kingston HERE !

4. Muskoka: Classic Cottage Country Vibes

Why Go: No list of Ontario road trips would be complete without mentioning Muskoka. Known for its picturesque lakes, cozy cabins, and family-friendly attractions, Muskoka is a quintessential summer destination that still shines in late August.

Highlights:

• Lakeside Cottages: Spend your days relaxing by the water, canoeing, or enjoying a lakeside BBQ.

• Waterfalls and Lookouts: Visit spots like High Falls in Bracebridge or the Dorset Lookout Tower for panoramic views.

• Small Towns: Explore the charming towns of Gravenhurst, Bracebridge, and Port Carling for boutique shopping, local eats, and scenic walks.

Tip: End your trip with a visit to one of Muskoka’s local farmers’ markets, where you can grab fresh produce and homemade treats to take home.

BONUS: Check out my three-day itinerary for a Muskoka getaway HERE !

Conclusion

Ontario’s diverse landscapes and charming communities make it the perfect destination for end-of-summer road trips. Whether you’re chasing adventure, relaxation, or a mix of both, these road trip ideas offer something for everyone. So, pack your bags, cue up your road trip playlist, and get ready to explore the beauty of Ontario before summer fades away!