Nestled Between Toronto And Detroit Is 'The Friendly City' With A Charming Downtown, Local Shops, And Art

When most travelers plan a trip to Canada, they tend to stick to the tried-and-true favorites. Places like Vancouver, Montreal, and Calgary are buzzing with tourists year-round, but what about the rest of the world's second-largest country? If you'd like to see a more under-the-radar side of Canada without missing out on convenient city amenities, Woodstock might be the perfect destination for you. Not only does it promise a charming downtown, local shops, and an impressive arts scene, but it's also within a two-hour radius of some of the country's most famous hubs, including Toronto and Niagara Falls (and there's a lot to do on a trip here besides seeing the waterfalls). Thanks to its welcoming atmosphere and impressive cultural scene, Woodstock is also known as "The Friendly City," promising a touch of warmth and a close-knit feel that would be hard to find in most of the major nearby hubs.

Being so close to the Canada-U.S. border, Woodstock can be reached by car, especially by those in western New York. Buffalo, for example, is less than a two-hour drive away. If a road trip is out of the question, you can take your pick of airports. Smaller regional airports in London and Waterloo are closest, but flights are limited. If you find a better route to Toronto Pearson International instead (76 miles away), you might want to read through this guide on how to avoid getting stuck at what is, without a doubt, North America's most stressful airport. On the flip side, the latter is the only option out of the three with a direct bus line to Woodstock. The ride lasts roughly 110 minutes.

One of Woodstock's biggest selling points is its cordial, inviting atmosphere. One Redditor offered a comprehensive roundup of why the city is a great place to live, saying, "Everyone here is friendly and welcoming, making it easy to make new friends and feel at home." They also rave about the year-round events, varied outdoor trails, and local businesses, all of which make for a good travel destination, too.

For visitors, most of the itinerary will be centered around downtown. The area is home to hundreds of charming, locally-owned shops and has free street parking for up to two hours, not to mention it's the site of many fun community events. Music in the Square is an easy one to catch if you come to Woodstock during the summer. Held in Museum Square, the concert usually starts at noon and lasts for two hours, making Thursday lunches that much more enjoyable. 

Speaking of lunch, there's a highly reviewed restaurant just around the corner from here: Finkle Street. It's Tripadvisor's top place to eat in Woodstock, featuring a contemporary, varied menu with dishes like wagyu burgers, wood-fired pizzas, free-range smoked Pekin duck, and special tasting menus. It's praised by customers for its service and timing, and the cocktails come highly recommended, too. Follow your meal with a cup of coffee and dessert from Early Bird, just a six-minute walk away. It's Woodstock's first coffee-roasting business, and their baked goods receive compliments from reviewers as well. For more of that Woodstock-type charm, plan a day trip to London. Located between Detroit and Toronto, this is Canada's "forest city" with family-friendly fun, tasty eats, and natural beauty. 

Those who like to shop, especially in smaller or second-hand establishments, will find penty to do in Woodstock. Foodies can start their tour with Cheesy Cow Company. They're known for their artisanal cheeses and meats, and many varieties are sourced locally. Their prices are generally considered reasonable, and they're located just a two-minute walk from the main square.  

Willing to venture a bit beyond downtown? Visit One of a Kind, the biggest antique mall in Canada. Spread over three floors and over 1,000 booths, this is a space where you'll find everything from jewelry, vintage accessories, and comic books to kitchenware, ceramics, and furniture sold by independent vendors. The mall gets 4.5 stars on Google, and it's located just under a mile from the town square.

Art lovers, on the other hand, can stop by Woodstock Art Gallery. It's located right across from Museum Square and features a collection of almost 2,000 pieces, many of which are created by local artists. Admission and parking are both free, but if you want to take the experience up a notch, you can enroll in one of their classes or workshops. The gallery is open from Tuesday to Saturday, from 10 a.m. to 5 p.m. (7 p.m. on Wednesdays). If you're more into the performing arts, add Theatre Woodstock to your itinerary. Audience members have complimented the comfortable set-up and helpful staff, and because the event calendar is pretty varied, there's a good chance you'll find something you'd like to see. Those who've got enough time left for a day trip might want to plan a visit to Kitchener, 45 minutes away. Hiding in Canada's lowlands, it's a German-inspired scenic city with famed festivals and markets.