Small Town Shopping in York Durham Headwaters

York Durham Headwaters is the ideal day trip destination for shoppers who love antiques and sweet boutiques. Ditch the heat and clamor of the big city in favour of the laid back pace and fresh air that comes with shopping in our sweet little villages.

Two guys window shopping

Your day trip begins with a scenic one-hour drive north of Toronto. Take your time and enjoy the scenery as it changes from concrete jungle to rolling green countryside to charming small town.

But which small town should you visit? Read on for insider tips on our three regions. Then set call your friends, set your GPS and set off for the ultimate shopping adventure!

Things to do in York

In eclectic Newmarket, you’ll score a range of treasures from fresh flowers to handmade jewellery and eco-friendly scooters! Georgina takes you back in time with an adorable general store and apothecary, as well as local gifts and art supplies. Shopping highlights in Unionville include handmade confections like fudge and chocolate, trendy boutiques and whimsical home décor.


  • Things to Do in Historic Newmarket

    In 1795, John Graves Simcoe took a trail along the Humber River that led him to the town we now call Newmarket. He started construction of Yonge Street,…
  • Top Things to Do in Historic Unionville

    Unionville’s Main Street, settled in 1794, is the ultimate in picturesque charm. Lined with seasonal decor and flowers, original historical buildings,…
  • Top 8 Things to Do in Historic Georgina

    Venturing outside the Greater Toronto Area for a break from the city and to discover more of Ontario is a great weekend activity. Head out to Georgina…

 

Things to do in Durham

Head to Bowmanville for unique gifts, home décor and the handicrafts of talented local artisans. For books, fashion and flowers, historic Uxbridge has you covered! And evoking the seaside shopping experience, Port Perry houses local fashion designers, goldsmiths, eco-friendly boutiques and miniatures.



Things to do in Headwaters

Downtown Orangeville has sinful shortbread, home décor and a jam-packed farmer’s market – and guess what? Broadway St. earned a People’s Choice award for best street in Canada! In Caledon, you’ll find unique clothing and gifts, art and craft pieces as well as a mindful spa experience. For the best antiques, head to Erin, where you’ll also find a fine chocolatier and the cutest boutique!


  • Top 10 Things to Do in Caledon

    Nestled between the Credit and Humber rivers, Caledon is a charming town. With a relatively newer history, the town and area surrounding it are full…
  • Top 10 Things to Do in Historic Erin

    Ontario is known for its charming small towns that lie outside of the GTA. With history, local businesses, and unique elements of fun, there’s always…
  • 10 Things to Do in Historic Orangeville

    Next time you find yourself itching for a mini road trip to a place you’ve never been before, Orangeville will hit the spot. What’s better than…

Stay connected

For the latest in shopping news, sign up for the YDH newsletter today!