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Walkable Downtown Windsor Winter Getaway

4 min Read

Walkable Downtown Windsor Winter Getaway

Located less than an hour from Halifax, heading toward the Annapolis Valley, Windsor boasts Ski Martock and a pedestrian-friendly downtown area brimming with cozy accommodations, tantalizing restaurants, a local brewery, provincial museum grounds, and a national historic site. A delightful mix of delicious cuisine and thrilling adventures awaits!

Outdoor Adventure

Hit the snowy slopes at Ski Martock and soak in the panoramic views of the Annapolis Valley from the peak. Martock proudly offers eight trails catering to all skill levels, from beginners to experts.

Ski Martock
Ski Martock

Perched above the town of Windsor is the Fort Edward National Historic Site. Established in 1750, Fort Edward played a pivotal role in safeguarding the passage from Halifax to the Annapolis Valley. Meander along the looped 1 km trail, marvel at the exteriors of the oldest blockhouse in Canada, and take in the expansive views that span the Bay of Fundy tides.

Fort Edward National Historic Site
Fort Edward National Historic Site

Enjoy a whimsical 20-minute walk through the walking trails at Clifton Museum Park, surrounded by ancient trees on this Provincial Museum’s property. While the museum itself is closed for the winter, the grounds and nature trails are accessible throughout the year.

Trails at Haliburton House Museum
Trails at Clifton Museum Park

Cozy Accommodations

After a day full of winter fun, check in to Geldert Guest House. This majestic three-story Queen Anne Victorian home, erected in 1898, gracefully intertwines vintage charm with modern elegance.

Geldert Guest House
Geldert Guest House

Select from one of three cozy guest rooms and enjoy the shared spaces, including a sitting room, parlour, and library. At Geldert Guest House, you’ll wake up to a fresh breakfast served in the dining room before you check out.

Breakfast at Geldert Guest House
Breakfast at Geldert Guest House

Or, stay at The August House, a boutique inn and gathering space in the heart of Windsor. Built over 170 years ago, this property was completely renovated in 2022 and today offers 11 modern guest rooms, intimate gatherings for up to 80 people and culinary events.

The August House
The August House

All rooms have their own private ensuite bathroom with heated floors. During your stay, you will feel taken care of in the beautifully designed and comfortable spaces. In the evening, unwind on the outdoor patio, warm up with a house-made hot beverage and charcuterie, or gather ’round a fire for the ultimate s’mores experience. A fresh and delicious breakfast awaits the next morning.

Relax at The August House

Places to Eat and Drink

If you’re looking for beer with class, look no further than Schoolhouse Brewery! Situated in Windsor’s lively downtown, Schoolhouse offers an inviting, school-themed taproom where you can sample an assortment of quality craft beers. They also serve a tasty menu and house-made non-alcoholic beverages.

Schoolhouse Brewery
Schoolhouse Brewery

Pay a visit to Hole in the Wall, a quaint and upscale restaurant with a menu that changes weekly. The gourmet pizzas and decadent desserts are fan favourites!

Hole in the Wall Restaurant
Hole in the Wall Restaurant
You can’t leave Windsor without stopping into The Spitfire Arms Alehouse, known for its welcoming atmosphere, delicious menu, and live music on weekends! There is also a heated alley for outdoor dining.
The Spitfire Arms Alehouse
The Spitfire Arms Alehouse

Make your way to Gerrish & Gray for a handcrafted latté, snack or full meal that you’ll want to sit and savour. Get cozy by the fireplace or enjoy the street facing windows. Be sure to visit for the weekend brunch!

Gerrish & Gray
Gerrish & Gray

Arts and Culture

Stroll Windsor’s Gerrish Street where you’ll find Mermaid Theatre. Housed in the historic Imperial Theatre, the company has won international acclaim for their unique staged adaptations of children’s literature, featuring striking puppets, innovative scenic effects, and original music. The theatre also hosts live dance performances, film nights, and concerts – make sure to look up show times before you visit.

All along Gerrish Street you’ll also find various shops, showcasing art and crafts by Nova Scotian and Atlantic Canadian artisans. If their creativity inspires you to unleash your own, head to Windsor Makers Studio & Art Market for a class. This community gathering spot offers classes in pottery, glass and textile arts. Their curated art gallery is also a great spot to pick up a piece for yourself and gifts to take home.

Windsor Makers Studio & Art Market
Windsor Makers Studio & Art Market

Wait there’s more! When you’re walking throughout Windsor’s downtown, see if you can find all 11 art installations.

One of the many murals in Windsor
One of the many murals in Windsor

Learn from the locals

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