There’s no denying that York Region is home to some incredibly charming main streets. Keep reading to learn how to plan your next visit to the most explorable main streets in York Region!

I love any opportunity I can get to drive along rural roads and find myself in a charming Ontario town. There’s something about looking out the window to see the leaves and landscape changing through the seasons, and small towns getting decked out for festivals and events each the year.
Ontario’s small towns and main streets are filled with storefronts changing their display windows, local coffee shops switching out their seasonal drink menus, and clothing and gift stores ready to welcome visitors with incredible finds. We’ve written a lot about some of the best small towns in Ontario here, but depending on where you’re located in the province, some of them may require a multi-day trip to enjoy them to the fullest.
Since a lot of our readers find themselves in the Greater Toronto Area, sometimes it’s nice to find a place that’s a little closer to home to visit, whether that’s for a few hours, or for a quick overnight visit. York Region, just north of Toronto, happens to have some incredibly charming main streets to to explore.
Whether you’re planning for a cute fall or winter day trip to hit the shops with a warm cup of coffee, or a bright, summery day spent patio hopping and enjoying the bustle of downtown, make sure you check out these main streets in York Region for your next local getaway.
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Newmarket: Dining, Shopping and Boutique Accommodations

Despite being a relatively large town and region, many people don’t realize just how charming the historic centre of Newmarket is. It’s a lovely place to walk around, and definitely one of the nicest main streets to venture on in York Region.
The best part of downtown Newmarket to explore is Main Street South, between Queen Street and Water Street. One of my favourite ways to explore a main street is to pop into a local coffee shop, and Metropolis Mercantile + Café is the perfect place to do that here. On the street level, you’ll find their bakery and cafe, and on the lower level you’ll find more cafe options, along with their mercantile shop. It’s a greenery-filled space, perfect for doing a little shopping and getting the day off to the right start.

From here, you’ll want to walk up and down Main Street and pop into more of its great shops. Downtown Newmarket has some incredible business owners who are always welcoming to new visitors.
If you need a little inspiration, Good Vibes on Main carries Life is Good clothing and accessories that will be sure to put a smile on your face. For cycling enthusiasts, BikeSports is a renowned independent bike shop in the province, carrying bikes and accessories with friendly staff to help you out if you’re in need of anything. And of course Flamingo Noir Record Bar is a fantastic place to come for music enthusiasts.
Consider grabbing a drink at Old Flame Brewing Company, or Overlea Restaraunt. Old Flame hails from Port Perry, and their location here on Main Street in Newmarket used to be the local fire hall. They have a merch shop and an extensive craft beer list, and while you’re able to bring outside food, they don’t have food service here–yet. Overlea is located on the rooftop of The Postmark Hotel, with beautiful views of the surrounding area. You can stay for a bite here, too, if you’re feeling keen.
The Postmark Hotel

Speaking of this hotel, if you’re looking for somewhere to rest your head while you’re exploring York Region’s best main streets, then you’ll want to book a stay at The Postmark Hotel. Opened by Archive Hospitality Group, the Postmark is the newest sister property to the Broadview Hotel and the Gladstone Hotel, both located in Toronto.
In true Archive fashion, they took an historic building in downtown Newmarket and breathed new life into it in the form of a boutique property. With 55 guest rooms, a lobby bar and restaurant, and a rooftop restaurant and event space, this is an exciting addition to Main Street.
It’s also worth nothing that the biggest drive-in movie theatre in the region, Stardust Drive-In, is just minutes away from downtown Newmarket and the Postmark Hotel. It makes for a fun way to end a summer evening here in the region.

A Village with Community Spirit: Schomberg
With its cozy, close-knit community, Schomberg is the smallest town on this list, and a truly lovely village to come to when you’re looking for a cute main street in York Region. When you visit, you’re going to want to focus on walking along Main Street between Western Avenue and Church Street.
Grackle Coffee is a fantastic place to start the day. Its a local coffee shop with a lot of heart on Main Street. They’re a bike-friendly property too, so for those coming on two wheels, you can count on there being many places to lock up at their bike rack. They also have an expansive patio for the summer months, and in the winter and fall their cozy indoor space is a treat to visit. It feels like a place straight out of Gilmore Girls.

Once you’ve grabbed a coffee, walk around town. Cottage and Crown, Heart in Home and Vintage Peony are excellent shops to visit. If you’re looking to go on a bit of a longer walk, the Roselena Drive Trail just south of town is a great place to go, too.
After walking around, I can’t recommend stopping at Schomberg Pub and Patio enough. It’s everything a pub should be, situated in an historic home with a tree covered patio to sit on during the summer months, and a cozy pub and dining space to enjoy indoors in the cooler months.
Unionville: Perhaps the Most Famous Main Street in York Region

Unionville’s Main Street is iconic for a reason. Often considered one of Ontario’s most beautiful towns, it’s served as the backdrop for TV shows like Schitt’s Creek and Gilmore Girls. All of the exterior shots in the pilot episode of Gilmore Girls were actually filmed right here in downtown Unionville.
By now you’re likely wise to my speed, but yes–if you’re looking to start the day with a delicious cup of coffee from a fantastic local spot, Behind the Alley is not only a beautiful space to do so, but their coffee is divine. It’s a Japanese-inspired gourmet coffee and matcha shop that carefully crafts each beverage. From smoking rosemary for an iced Americano to serving up cold brew in wine glasses, you won’t regret starting your time in town here.
After caffeinating, wander up and down Main Street. The best parts to roam along Main Street Unionville are between Carlton Road and the Unionville Train Tracks, near the Unionville Train Station Community Centre. Some places worth visiting are the Old Firehall Confectionery and Unionville Candle Co., the Varley Art Gallery (which offers free admission to visitors), or you can go for a walk around nearby Too Good Pond.

If you’re looking for a place to sit down for lunch or dinner while you’re in town, there are several places in Unionville that are considered some of the best restaurants in Markham, which you are welcome to check out.
Small Town Charm and Canadian Art in Kleinburg Village
Located in Vaughan, Kleinburg’s historical district runs along Islington Avenue and is filled with charming places to stop and historic buildings to admire.
To start off your time walking along Islington Avenue, pop into Balzac’s Coffee Roasters for a quick coffee, and to enjoy this location’s historic setting. Balzac’s always does such a great job finding historic locations across the province, and their location in Kleinburg is no different. They completely restored the Arthur McNeil house, which is a landmark heritage property in the heart of town that had fallen into disrepair. If it’s a nice temperature outside, sitting outside on the wraparound porch here is always a good decision.

Another great place to come for coffee or a more significant brunch or lunch is the Kleinburg Kafé. They have welcoming indoor and outdoor seating areas, and their menu features dishes like Avocado Toast, Homemade Meatballs and sandwiches, among other things.
After lunch or brunch, continue walking along Islington Avenue and pop into shops and stores along the way. Old Firehall Confectionary is a favourite, the sister property to their flagship location in Unionville. Gwen Art Gallery is another beautiful place to pop into. Not only is it an art gallery, but it’s in a unique historic building in town.

It wouldn’t be a trip to Kleinburg without a visit to the famous McMichael Canadian Art Collection. On top of being a beautiful museum filled with artwork by the Group of Seven and many more Canadian and Ontarian artists, it’s located in a beautiful setting and is connected to the extensive Humber River trail network, making it a must visit for both art and nature lovers.
Visit These Towns to Show Your Love of York Region
Whether you’re looking for a cozy fall day trip, a winter escape, or a summertime jaunt, York Region’s main streets offer the perfect blend of history, community, and undeniable charm. So grab a coffee, take a stroll, and experience these four beautiful towns and their historic main streets for yourself!
Bri Mitchell was hosted as media by Central Counties Tourism to cover her experience in these towns. All opinions expressed are completely her own.
Bri Mitchell is a travel writer and content creator from Toronto, Ontario. She loves to highlight all things nature, food, wellness, history and adventures in her work. Bri writes and shares her travel experiences from across Canada and beyond on Instagram and TikTok @brimitchelltravels, and in her articles for travelingmitch.com, Ultimate Ontario, and here on We Explore Canada.