Autumn in Ontario is the perfect time to gather your friends and set out on a relaxed adventure filled with new-to-you neighbourhoods, tasty meals, historic landmarks, and fabulous fall colours. Add overnight accommodations at some off-the-radar gems, and you’ve got a foolproof formula for fun times with friends.
Day 1
Morning: Hamilton
Celebrate your friendship by raising a mug of delicious coffee at your first stop of the trip, The Cannon. This character-filled coffee shop is located in the heart of Hamilton’s Ottawa Street district, an area renowned for its vibrant arts and culture scene.
Once your crew is sufficiently caffeinated, take some time to stroll along Ottawa Street. Snap some selfies in front of the colourful street murals, including the Ottawa Street Orca at 189 Ottawa Street N. and the Caro Restaurant Mural at 4 Ottawa St. N. Browse your way through any of the dozens of eclectic shops that capture your attention.
Next, visit Dundurn Castle National Historic Site, an incredible 19th-century mansion that offers a glimpse into Hamilton’s history. Explore the opulent rooms and the kitchen garden as you learn about the castle’s intriguing past through stories about the family who lived above the stairs and the servants who worked below.
AFTERNOON: HAMILTON
All of the morning’s steps will have helped you and your crew work up an appetite for lunch. Fuel up for the afternoon at Brewers Blackbird Brewery and Kitchen, a friendly craft brewery and restaurant in Ancaster known for its handcrafted brews and delicious comfort food. If your lunchtime pint leaves you curious to try other brews made in the area, consider following the True Brew Path and trying out places like Shawn & Ed Brewing Co. and Fairweather Brewing Company.
After lunch, spend some time discovering another charming neighbourhood nearby, downtown Dundas. This Dundas and Ancaster Fall Guide will help you plan your stops in advance. When you’re all shopped out, check into a cozy inn or bed & breakfast, like The High Acre or The Homestead 1867 Bed and Breakfast, to drop your loot and prepare for dinner.
EVENING: HAMILTON (DUNDAS)
As the sun begins to set, head to Quatrefoil Restaurant for a meal you’ll all remember for years to come. This award-winning restaurant offers a menu inspired by seasonal ingredients and a carefully curated wine list to complement its contemporary French cuisine.
DAY 2
MORNING: SIX NATIONS – OHSWEKEN
Start your day at Jax Sweet Shoppe, a cozy café known for great coffee, an excellent breakfast menu and a friendly retro atmosphere.
Then, hit the highway, and when you enter the Six Nations of the Grand River, stop at Chiefswood National Historic Site, the childhood home of renowned Mohawk poet E. Pauline Johnson. This historic home offers a fascinating glimpse into Canada’s rich Indigenous roots.
Continue your Indigenous education with a visit to Iroqrafts, a unique store specializing in First Nations arts and crafts. The extensive collection of handmade jewelry, pottery, and traditional artwork will leave you wanting to take home a few souvenirs!
AFTERNOON: PARIS & SIX NATIONS
Follow the Grand River into Paris at lunchtime and discover Cobblestone Public House. In addition to a delicious lunch, you’ll be treated to picturesque views of the river and the town’s beautiful heritage buildings.
After lunch, gather your gang for a colourful fall paddle on the Grand River. Outfitters like Grand Experiences make it easy to get set up with all the gear you need to canoe, kayak or raft your way down the Grand. They’ll even provide a guide if you’d prefer a little extra support.
Pair your paddle with a cozy night in one of the luxurious group camping cabins at Chiefswood Park. The log cabins, set within a beautiful Carolinian forest, have been designed to match authentic local culture and history while providing a rustic yet modern stay.
EVENING: PARIS
After settling in at your cabin, head back to Paris for dinner at Juniper Dining Co. The restaurant also offers takeout if you’d prefer to dine in the comfort of your cozy cabin.
If you’ve timed your trip right, spend the evening taking in a concert, comedy show or other live performance at the Sanderson Centre for the Performing Arts before calling it a night.
DAY 3
MORNING: OHSWEKEN & MILTON
Fuel up with a hearty breakfast at Burger Barn. In addition to its namesake burgers, which have been featured on Food Network Canada’s You Gotta Eat Here, the restaurant also has delicious breakfast options available all day.
After breakfast, head to Kelso Conservation Area, where you can choose between a leisurely hike or a breathtaking chairlift ride up the Niagara Escarpment to witness the incredible fall colours.
While in this area, a stop at Springridge Farm is a must. Browse the selection of local produce, homemade treats, and unique gifts, and get a taste of what fall on the farm in Ontario is all about!
AFTERNOON: OAKVILLE
For lunch, make your way to Glen Abbey Golf Course for a memorable meal at one of Canada’s most famous golf courses. Your lunch at The 18 is served with a fabulous view of the course’s 18th hole.
Conclude your trip by exploring Oakville’s Gairloch Gardens, a property filled with meticulously manicured gardens that two different prominent Oakville families once called home.
