From Market Days to Curtain Calls:
A Weekend in St. Jacobs

by Christine Wilson | August 2026

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• Make a day trip to St. Jacobs into a weekend getaway.
• Experience professional theatre in St. Jacobs at Drayton Entertainment’s St. Jacobs Country Playhouse or Hildebrand Schoolhouse Theatre.
• Explore the best of fall with market days, village charm, changing leaves, harvest scenery and plenty of reasons to slow down and stay awhile.
• Enjoy big-city entertainment without the big-city stress in a charming village setting just over an hour from Toronto.

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St. Jacobs has a reputation for being a daytime destination. Come for the St. Jacobs Farmers’ Market, browse the shops in the Village of St. Jacobs, grab lunch, and then head back home. 

But stay a little longer and you’ll discover a different side of the village.  

After the market stalls close and the afternoon winds down, there’s still plenty of reason to stay and explore. Grab a dinner made with fresh local ingredients, stroll the village as the crowds thin out, then settle in for an evening at the theatre, turning a day trip into a proper weekend away.

Drayton Entertainment has two of its six Ontario venues in St. Jacobs: the St. Jacobs Country Playhouse in the Market District and the Hildebrand Schoolhouse Theatre in the village. Both offer professional productions in settings that feel distinctly connected to their surroundings.

“It’s a theatre experience that feels both local and professionally scaled,” says Steven Karcher, Executive Director of Drayton Entertainment. “Audiences have access to productions they might otherwise have to travel to Toronto or another major city to see.”

Theatre rooted in the St. Jacobs experience

Drayton Entertainment’s approach is to make the theatre visit part of a larger destination experience.

“Our theatre model is predicated on having audience members travel specifically to attend live theatre performances, and combining those visits with local dining, shopping, accommodations, and other attractions,” Karcher explains.

St. Jacobs lends itself naturally to that kind of getaway. Its village, world-renowned market, and charming countryside surroundings give visitors plenty to explore during the day, while a performance gives the evening a clear focal point. Instead of fitting everything into a few hours, you can really slow down and soak up the region by spending the night.

The character of each venue adds another layer to the experience. The St. Jacobs Country Playhouse features timber architecture inspired by traditional Mennonite post-and-beam construction. Meanwhile, the Hildebrand Schoolhouse Theatre occupies a restored 1867 schoolhouse with an intimate, cabaret-style atmosphere.

“Unlike large urban theatres, our St. Jacobs venues reflect the character of the community itself,” Karcher says. “These are two very different experiences, but both provide a setting that feels authentic and uniquely connected to the area’s history and traditions.”

For visitors coming from a larger city, that means you still get a polished professional production, but in the setting of a quaint village rather than a bustling downtown entertainment district.

What’s on the calendar for Fall 2026

Fall brings another reason to make the trip. The farms around St. Jacobs are in full harvest swing, the leaves are changing colour, and cooler temperatures make it comfortable to spend the day outside. It’s a season that suits the pace of the area, with fewer summer crowds and plenty of opportunities to explore the area without rushing from one stop to the next.

It’s also a strong season for Drayton’s lineup. This fall, Into the Woods brings Stephen Sondheim’s modern classic to the stage, following familiar fairy tale characters as they discover what happens after “happily ever after.” Jonas and Barry in the Home offers a Canadian comedy about two senior citizens navigating life in a retirement residence.

Then, as the holiday season approaches, Snow White and the Seven Tenors puts a modern spin on the familiar story with music, comedy, audience participation, and family-friendly fun. All is Calm: The Christmas Truce of 1914 takes a more reflective turn, telling the true story of the Christmas Eve ceasefire between British and German soldiers during the First World War.

The variety is part of Drayton’s appeal. Its programming spans Broadway musicals, comedies, dramas, jukebox revues and family pantos, all presented in intimate venues.

A night out with big-city polish and small-town charm

What makes the St. Jacobs experience compelling is the balance. You can see a professionally produced show without dealing with the traffic, crowds, and logistics that can turn a night out in a larger city into an undertaking.

At the same time, St. Jacobs hasn’t been stripped of the qualities that made it a destination in the first place. 

“There is a sense of authenticity in St. Jacobs that’s increasingly hard to find,” Karcher says. “The village celebrates its Mennonite heritage, local entrepreneurship, and agricultural roots while offering modern amenities and cultural attractions.”

That authenticity is what ties the whole weekend together. The production may be the kind of thing you would normally travel to a major city to see, but here it becomes part of a much more relaxed getaway.

You get the quality of a big-city night out, without the big-city stress.

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Reconnect with St. Jacobs

With festive flavours, local charm, and something new around every corner—St. Jacobs is the place to be this season.

Discover more to do and see this Fall and Holiday Season in St. Jacobs!