Fall in Ontario means changing leaves, road trips, and sampling the flavours of the season. This year, travel blogger and Ontarian abroad, Natalie DiScala of the blog Oh Travelissma spent an extra special weekend showing off what fall in Ontario is all about to her American husband Johnny (of JohnnyJet.com) and their two-year-old son Jack.
From trying butter tarts for the first time, to discovering luxury in the country at Hockley Valley Resort, their tour of York Durham Headwaters was a celebration of all things fall.
Here are a few of their suggestions for must-see stops on your fall road trip.
NATALIE’S PICKS
LANDMAN GARDENS & BAKERY
“Landman Gardens & Bakery offers something for everyone. The most unique thing about it is definitely the Blackhouse that’s on the premises. A Blackhouse is a small, traditional stone house typically found in the Scottish highlands. It looks like something straight out of a movie and can be booked for private dinners. The farm was most exciting for our son, who couldn’t get enough of all the goats, pigs and chickens and I was in heaven inside the bakery, where the aroma of freshly baked pies made with farm-fresh ingredients lingered heavily in the air. We went home with our arms full of Thanksgiving pies and a box of butter tarts. My American husband had never heard of, let alone tried, this Canadian staple so we had to remedy that quickly. He tasted his first butter tart at Landman Gardens & Bakery and it was love at first bite!” – Natalie
GRAND SPIRITS DISTILLERY
“Situated in Grand Valley, Ontario, inside a schoolhouse from 1892, Grand Spirits Distillery is a charming homage to the past, yet very much present-day in everything about it – from its custom-made Steampunk Still to its contemporary menu of food and drink. Under the direction of acclaimed Chef Martin Kouprie, the menu features local, seasonal fare that is inspired by the food of the 1920s, but thoughtfully updated to please the discerning palates of today’s visitors. After touring the distillery and photographing the beautiful still from every angle, you’ll definitely want to stop and eat in the speakeasy-style dining room.” -Natalie
SPIRIT TREE ESTATE CIDERY
“The orchard at Spirit Tree Estate Cidery was at its peak when we visited in early October and the apples were ripe for the picking! The picking season in Caledon runs from early September until the end of October, and typically includes Cortland, McIntosh, Gala, Golden Delicious and Ida Red apples. Inside, cider is made downstairs, while upstairs, the Ciderhouse Bistro is a busy and popular spot for lunch and dinner. And as you might expect, the menu is full of quality, locally-sourced ingredients.” – Natalie
JOHNNY’S PICKS
HOCKLEY VALLEY RESORT
“I don’t know if they light fires all year round but the moment I stepped out of the car, I smelled burning wood, just like you do when you’re at a ski lodge in the middle of the winter. The fire transported me to when I was just a little lad growing up in Connecticut, when my dad would light fires in our fireplace on cold winter days.
The resort also has an 18-hole championship golf course, designed by renowned Canadian golf course architect Thomas McBroom. The course boasts some of the most breathtaking vistas in southern Ontario. It’s open to the public with rounds beginning at $60. You can reserve tee times online.” – Johnny
ADAMO ESTATE WINERY
“Just two minutes up the road by car is the resort owner’s Adamo Estates Winery. On weekends and for special events, the Hockley Valley Resort offers a free shuttle for the three-minute drive. The 25-acre vineyard has 23,000 vines and includes a 20,000 square foot facility for production, wine tastings and retail sales. Tastings are offered daily and no reservations are required. Public tours are available Saturdays and Sundays at 12pm and 3pm. Single tastes start at just $3.” – Johnny

BONUS: JACK’S PICK!
DOWNEY’S FARM
“We ended our grand tour of this gorgeous Ontario region at Downey’s Farm, where the first thing we saw when we pulled up was an enormous pumpkin patch that my son just dove into and could barely be pulled away from. It was the perfect spot for some fall family photos! There’s lots to do at Downey’s Farm – there’s a farm (obvs!), a market, a winery … but we headed straight to Pumpkinfest, which is packed with fun things for kids to do – from wagon rides and puppet shows to jumping pillows and duck races! Jack couldn’t get enough of Goat Mountain Slide and we all had fun traipsing through the 8-acre corn maze. A friend recommended picking up some of Downey Farm’s famous pumpkin doughnuts for our ride home and we completely forgot so I guess that means we definitely need to go back!” – Natalie
Want to recreate Natalie, Johnny and Jack’s adventure in York Durham Headwaters? They followed a family-friendly version of the Temperance and Temptation Self-Guided tour. Get the guide here. Happy Travels!