Windsor Nova Scotia Travel Guide
Exploring Windsor Nova Scotia | A Complete Guide to Things to Do & See
When it comes to underrated Nova Scotia travel destinations, Windsor is a rising star. At the intersection of the Avon and Annapolis valleys, Windsor offers an unforgettable and underrated experience where maritime charm, rich history, and wine country collide. Whether you’re craving a quiet retreat surrounded by nature or a heart-thumping adventure, Windsor Nova Scotia is a great pick. Here is my ultimate guide to Windsor Nova Scotia.
Best Time to Visit Windsor
Peak season in Nova Scotia is July & August (and into early September) but the fall is the best time to Windsor. I recommend late September or early October to get the best travel experience. Seasonal businesses are still open and the peak season crowds have died down. Beyond the benefit of fewer people, fall in Nova Scotia is spectacular, the temperature is mild, and it’s the perfect time to take advantage of what Nova Scotia is known for — outdoor adventure and wine country!
Getting Around Windsor
You’ll need a car – there’s no way around it. Public transportation isn’t available in most regions of Nova Scotia so if you’re planning to leave Halifax (which you should), you’ll need to rent a vehicle. Travel by car is easy in Nova Scotia. There are no large highways and traffic is always light, compared to other places in the world. I would recommend a mid-size vehicle if you’re planning on any rural exploration like hiking or exploring our many hidden beaches. An SUV is a great option because you’ll have the clearance to navigate back-rounds and off-the-beaten-path excursions.
Where to Stay in Windsor
Windsor has some truly incredible accommodations. From historic inns to luxury Airbnb options and everything in between. You can’t go wrong with any of these options:
Where to Eat and Drink in Windsor
For a small town, Windsor has a surprising collection of dining options, including a brewery, bakery, distillery, and multiple restaurants.
Gerrish & Gray Cafe
Garrish & Gray would be my top pick for breakfast or brunch in Windsor. They offer a homey, casual dining experience and prioritize locally sourced ingredients.
Bedards Bakery
Go where the locals go. That’s always my advice! When we visited Windsor, every local we met told us to visit Bedards – so we did. They offer a variety of breads, pastries, and cakes, all made from scratch with natural ingredients and the line-up out the door told us everything we needed to know. It’s a must-visit on your list. Note: at the time of this article, their hours of operation are limited to only a few days a week.
Schoolhouse Brewery
Schoolhouse is a unique school-themed taproom and kitchen in Windsor and also happens to be one of our favourite places to visit on every trip. They’re an award-winning brewery with great beer and seltzers on tap but they also offer a tasty menu as well (I recommend the classy fries). Their vibe is casual, comfortable and inviting – plus, their patio is dog-friendly!
Avondale Sky Winery
Avondale Sky is a special place. It’s a church-turned-tasting room located in the Avondale Sky vineyard. They offer wine tastings and an exceptional food menu inspired by the wine regions around the world. They’re only open seasonally, so be sure to visit between May and November.
Hole in the Wall
With a large menu to choose from as well as their one-a-month destination dining experience, Hole in the Wall is a great dinner option. They offer indoor and outdoor dining as well as weekly changing menus.
Meander River Farm
A little off the beaten path but worth a visit, this cidery in Newport is lovely. They’ve got some fabulous ciders to try, beautiful gardens to enjoy and if you’re lucky the resident wolfhounds will be on site for a visit (they’re sweet, gentle giants).
Spitfire Arms
Windsor’s go-to pub, Spitfire Arms offers a blend of traditional British fare and North American favourites. They have a large menu with some really interesting bites and brews. This casual pub is a warm and welcoming place to grab a meal and also offers a truly unique outdoor dining option that’s based on the cobblestone street restaurants in Europe.
Cherry Tree Distillery
Cherry Tree is a speakeasy tasting room and craft micro-distillery that specializes in small-batch artisan Gin. Their 1920s-style cocktail tasting is an unforgettable experience!
Bent Ridge Winery
Located directly across from Ski Martock, Bent Ridge is one of Nova Scotia’s wineries and offers a unique Italian and Latin-inspired menu and decor. Their wood-fired pizzas are a great reason to visit and the ambiance is exceptional.
Top 5 Things to Do in Windsor
1. Have lunch at Avondale Sky Winery
Avondale Sky winery is a special place (as I’ve said) but it’s more than just a beautiful setting with great wine and food. This family-owned and run winery is so warm and welcoming that you’ll feel like part of the family the moment you walk through the doors.
2. Visit OnTree Park for a Treetop Adventure
OnTree park is an arial adventure park, but don’t let that intimidate you. The courses range from very easy to very difficult so you can choose what’s best for you.
3. Dine with the Dinosaurs
Picture this — you arrive at a secluded beach at dusk, and stroll down a tree-lined path to the water’s edge where you’ll find a romantic charcuterie dinner set up and waiting for you. You’ll sit on cozy pillows and dine as the sun sets. This is a spectacular experience that everyone should have at least once!
4. Visit the Hants County Exhibition
You’ll have to time this one right — the exhibition runs for a couple of weekends in September and is full of things to do. As the Oldest Agriculture Fair in North America, you’ll find a midway full of rides and games, a variety of food vendors, live music and the main events like barrel racing, and tractor pulls.

5. Book a Private Wine Tour
Wolfville is the mecca for wine tours in Nova Scotia but Windsor is a sneaky little option that not everyone knows about. Vintage Vino Wine Tours will pick you up at your accommodation and create a custom wine tour of the valley for you. One of the many benefits to this kind of tour is that it’s private! So you can explore Nova Scotia’s wine region, without the rowdy bus crowds!
Other Things to See and Do in Windsor
1. Hike to Ettinger Falls
The hike to Ettinger Falls is an easy one but, in this case, effort in doesn’t equal the reward! The falls are stunning. There is a gate on the road that is usually open, but there is a warning it could be closed at any time, so it’s best to park at the gate and walk up the road. The trail to the falls is at the top of the hill and easy to spot. A short walk in the woods will take you to the top.
2. Go Horseback Riding
Warning: Evangaline Trails is a very quirky “business”. They don’t use technology which means the only way to book is by phone. We’ve been twice and find the process quite frustrating but they’re also very straightforward in telling you that customer service isn’t their forte. Be aware that you’ll receive very little information (like road closures on the main access point that they don’t tell you about). The bedside manner is “rough”, to put it nicely but the actual horseback riding experience is pretty fun.
3. Eat a Croissant at Bedard’s Bakery
As mentioned earlier, this is a local favourite for good reason. The croissants are fabulous – nothing more needed here!
4. Sample 1920’s Cocktails at Cherry Tree Distillery
A trip to Windsor isn’t complete without visiting Cherry Tree Distillery and experiencing their cocktail samples. You’ll be transported back to the roaring 20’s with the decor and the drink samples.
5. Go Apple Picking at Daniel’s U-Pick
Conveniently located on the grounds of Bent Ridge Winery, the U-Pick is a fun activity for the whole family.
6. Visit the Giant Pumpkins at Howard Dill’s Farm
The Dill’s farm is famous for its giant award-winning pumpkins. It’s important to note, however, you’re no longer allowed to enter the patch and see the pumpkins up close. We get it, not everyone has respected the property, but it’s a shame because there’s not much else to do at the farm.
7. Explore the Haliburton House Museum
Walk the scenic grounds among the giant willow trees as you wind your way up to the museum. Once inside, you can image Victorian Windsor as you explore the house, where Haliburton created his claim to fame:the fictional Yankee clock pedlar, Sam Slick.
8. Visit Fort Edward National Historic Site
Explore North America’s oldest military blockhouse and a key chapter of Canada’s colonial history high above Nova Scotia’s historic Minas Basin in Windsor. Built in 1750, Fort Edward provided an important British stronghold during decades of discord with Acadian settlers and the Mi’kmaq people.
Know Before You Go
Like many rural communities, hours of operation can vary greatly. It’s not uncommon to find restaurants and shops closed on certain days of the week so be sure to call ahead. I would recommend not relying on Google hours in these communities because they’re not always updated. Your best bet is to call ahead and check.
* We were guests of Nova Scotia tourism for this trip — as always, all opinions and oodles of photos are our own. We never guarantee positive reviews to partners and only share what we think you’ll love! Happy exploring! *