Wonderful Weekend in Stratford Itinerary for a Multi-Generational Trip

I mostly travel solo but sometimes I get the opportunity to set off on an adventure with my father. I still remember when I took him overseas for his first time and saw his eye’s delight in the wonders before him and his mouth agape in awe. That trip helped me see Europe in a new light. And that’s why I think multi-generational travel is so important. Whether you’re traveling with your aunt or one of your parents, you both see the world through a different lens because of the time you grew up in, what you were exposed to and so many other factors.

So, when I got the opportunity to travel to Stratford with my father I was beyond thrilled. It’s one of my favourite Ontario destinations and I couldn’t wait to show him my favourite places in Stratford and discover new ones with him. And just because we come from widely different eras it doesn’t mean multi-generation travel can’t be fun. So I put together the perfect multi-generational Stratford Itinerary to help you and your loved ones enjoy a wonderful weekend in Southern Ontario’s premier arts town.

Planning a Multi-Generational Vacation to Stratford

Stratford City Hall

There are so many things to do in Stratford for every traveler, whether you love exploring the outdoors or art galleries. And one of the best things to do, and what draws people from across the globe, is to attend the Stratford Festival. During you’re weekend in Stratford I recommend taking in two different plays. During my recent visit, my father and I took in two plays, Little Shop of Horrors – which was a cult classic for my father’s generation, and The Neverending Story – which was a popular movie from the early 80s when I was a kid.

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Another recommendation is to do a little research before you planning your Stratford itinerary, check out some of the incredible restaurants, pubs, and diners that you can eat at during your stay. Try choosing a few yourself and have your father, or whoever you’re traveling with choose a few. You won’t be disappointed in any choice you make. But a few of my favourites include: for lunch try Madelyn’s Diner, Keystone Alley or Jobsite Brewery for dynamite pizza and for dinner try Bijou Restaurant, Boar’s Head Pub or Revival House which is set in an old church.

Jobsite Brewery

Below you’ll find my suggested Stratford itinerary for your multi-generational vacation. You can follow it to the tee or use it as a rough guide to help you plan the perfect weekend in Stratford. But whatever you do, enjoy yourselves and take time to cherish each other’s company and maybe even learn a thing or two about each other.

3 Day Stratford Itinerary

Friday – Day One

Stratford-Perth Museum

Arrive into Stratford mid-morning and head over to the Stratford-Perth Museum. A visit to the museum is the perfect way to start your Stratford vacation as you’ll learn all about Stratford, the area’s history, learn about the beginnings of the Stratford Festival and more.

Afterward, head into downtown Stratford for lunch before your play. Afternoon performances run at two o’clock, so you’ll have plenty of time to enjoy lunch and get excited for your play. If you still have time before your play be sure to pop into the Festival Shop, there’s one beside the Avon Theatre and one across from the Festival Theatre. Browse the fun Shakespearean merchandise and grab a souvenir from the play you’re seeing.

Stratford Festival merchandise

As the crowds dispense from the theatre all abuzz with excitement consider taking in one of the awesome foodie trails that Stratford Tourism offers. There’s the sweet Chocolate Trail or the fun Bacon & Ale Trail. You can purchase your vouchers and trail guide online or pop into the Tourism office located across from City Hall. The trails cost $30 and come with a trail guide of all the establishments in Stratford, and area, where you can use the 5 vouchers you get with the package.

Bacon & Ale Trail at Boar's Head Pub

If you opt for the Chocolate Trail be sure to head to Rheo Thompson Candies, Revel and Junction 56 Distillery for tasty treats. But if you choose the Bacon & Ale trail you’ve got to try Madelyn’s Diner’s half-pound butter tart filled with savoury local bacon, Black Swan Brewery for a flight of local beer, and Boar’s Head Pub for a pint and delicious appetizer. These trails make for a fun way to explore Stratford’s shops and restaurants. It’s like an adult scavenger hunt with a treat at the end!

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After some exploring and shopping enjoy a nice relaxing dinner at one of the outstanding restaurants in Stratford.

Saturday – Day Two

multi-generational travel in Stratford

Morning in Stratford is the best time to explore. So, after a refreshing breakfast at your hotel or Bed & Breakfast head over to Totally Spoke’D to rent some bikes – or if you’re adventurous a tandem, and enjoy a relaxing bike ride along the Avon River that runs right through town. Stop at all the beautiful parks and gardens that dot the river, from the Shakespearean Gardens to the Arthur Meighen and Ted Blowes Memorial Peace Gardens beside Festival Theatre.

Gallery Stratford

While you’re here pop into the Gallery Stratford to browse their awesome exhibits, admission is free but donations are appreciated. After a browse around the gallery, be sure to take a closer look at the exterior. The Gallery is housed in the city’s old pump house, built in 1883.

Head back downtown to return the bikes and make the tough decision on where to go for lunch. If you’re looking for something light try one of the many great cafes that dot Stratford’s downtown, like Edison Café, Revel or the original Balzac’s.

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Stratford Garlic Festival

If you can, try and plan your Stratford trip around one of the countless festivals that happen all year long. As fall in Stratford is my favourite time of year, I recommend visiting during the Garlic Festival, the weekend of the Fall Fair, or for the Stratford Lantern Parade.

If there aren’t any festivals or events going on during the weekend you’re there you could indulge in more of the food trails, pop into a few of the amazing art galleries downtown, or head just outside of town to explore one of the neighbouring small towns bursting with personality like Millbank, Shakespeare, or St. Marys, all of which are within a twenty-minute drive from Stratford.

Avon Theatre

Fuel yourself with a delicious dinner before your last play in Stratford. (Night performances are at 8pm) One of my favourite things to do after taking in a play is to talk about it. So, on your way back to your hotel discuss what you loved about the play, what inspired or touched you. You may be surprised that you both have similar takeaways from the performance. Just because you may be one or two generations apart the Stratford Festival has a way of bridging that gap.

If you’re looking for more things to do in Perth County there is a wealth of outdoor activities, small towns to explore, tasty farm gates, and something for everyone – from solo travellers to families!

Sunday – Day Three

Stratford's Slow Food Market

It’s your last day in Stratford and I hope you squeeze in a few more hours of exploring before returning home. Head to Stratford’s Slow Food Market, located in Market Square behind City Hall, for some local produce, tasty treats to bring home and other local vendors.

Take one last loop around downtown, visit some of the great artisan shops like Distill, Meet Your Maker and Got it Made. And don’t forget to use up the last of your vouchers from the food trail you chose. And if you still have some time take a stroll through the T.J. Dolan Trail that can be accessed from downtown or rent paddle boats from Avon Boat Rentals and see Stratford from a new perspective. Enjoy a dose of nature and stretch your legs before you jump in the car to drive home.

Where to Stay in Stratford

The Canadian Suite at the Forest Motel

Stratford has a wide range of accommodation, from charming Bed & Breakfasts to motels that offer everything you need. So when you’re planning your vacation in Stratford and looking for where to stay with your older family member here are a few great options. If you both enjoy a little peace and being outdoors, consider staying at the Forest Motel. Located a ten minute drive from downtown Stratford, the Forest Motel offers suites that have multiple rooms for privacy, a kitchenette, lounge and more. Plus, it’s situated on a picturesque property that has a lake you can canoe on, trails to hike or even bikes to rent to get into town.

Mornington Rose Bed and Breakfast exterior

Another great option for where to stay is one of the numerous Bed & Breakfasts. In my opinion, Bed & Breakfasts are perfect for multi-generational travel. You always meet a wide range of interesting people from all over that also range in age, and they’re great for the social aspect – especially around the breakfast table. One of my favourite B&B’s in Stratford is Mornington Rose Bed & Breakfast.

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So, grab your mother, father, aunt, grandfather, or the entire family and get planning your multi-generational Stratford itinerary today!

I was a guest of Visit Stratford but as always all opinions expressed are my own.

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3 Day Stratford Itinerary for an Amazing Multi-Generational Trip
Stratford Itinerary for a Multi-Generational Vacation

Stephanie

I'm a Canadian gal with a passion for travel, the great outdoors as well as coffee and books. I hope to inspire others to feel the same way! Traveling mostly solo, I love to explore my own backyard of Ontario as well as exotic cities around the world.

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