Windsor

Travel Guide

A welcome sign at Cradle of Hockey, Long Pond, Windsor, Nova Scotia.

This essential stop in Nova Scotia is full of attractions that show both its agricultural and maritime personalities. Hockey may have been invented here too.

As you drive through the vast plains surrounding Windsor, you may detect a hint of ocean air in this otherwise agricultural area. Windsor was first established by 17th-century Acadians who grew crops particular to its marshy climate. Strategically near a harbor and a railway, the town became a hub for shipping. A booming economy brought the construction of stately homes, many of which still line the town’s handsome streets. Walk through this Atlantic Canada architectural treasure and see for yourself.

For some family fun, visit Howard Dill Farm where you can view perhaps the biggest pumpkin you will ever encounter. Ride an impressively accurate miniature train at the Trecothic Creek & Windsor Railway. In late summer, get lost in the yellow of Dakeyne Farm’s Sunflower Maze. 

Windsor is foremost known for proudly claiming itself the birthplace of hockey, although other towns make the same claim. Visit the Windsor Hockey Heritage Museum and peruse its fascinating reconstruction of early hockey activities. Learn about hockey’s ancestor game, hurley, and about the writer who first witnessed a group of boys playing it on a frozen pond. 

Windsor has many good restaurants, ranging from English-style pubs to Atlantic Canada bistros and dessert stores. Along with hotels and motels, Windsor has cozy, one-of-a-kind accommodations.  

Except for the Dill and Dakeyne farms, most attractions in Windsor are within walking distance of each other. Fly into Halifax International Airport and rent a car for the 50-mile (75-kilometer) drive to Windsor. There is also a bus service that connects the town to many destinations in the area.

Many visitors come to Windsor for a peaceful weekend retreat. With the geologic marvels of the Bay of Fundy and Nova Scotia nearby, however, you may decide to extend your stay in Windsor to explore farther afield to enjoy Nova Scotia’s natural wonders. 

The August House

The August House

3.5 out of 5
494 King St Windsor NS
The price is ¥22,883 per night from Oct 13 to Oct 14
¥22,883
¥27,328 total
Oct 13 - Oct 14
includes taxes & fees
Stay at this guesthouse in Windsor. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
9.8/10 Exceptional! (221 reviews)
"The owners have obviously poured a lot of time, effort and love into the property. Breakfast was superb, with everything from egg bites to prosciutto and yogurt, and many things gluten-free. Bathroom was excellent and heated floor much appreciated. One suggestion: Those with tricky backs and knees ..."

Reviewed on Sep 10, 2026

The August House
Gateway to Annapolis Valley | Windsor Studio Suite

Gateway to Annapolis Valley | Windsor Studio Suite

Windsor NS
The price is ¥16,146 per night from Sep 15 to Sep 16
¥16,146
¥26,360 total
Sep 15 - Sep 16
includes taxes & fees
Stay at this apartment in Windsor. Enjoy laundry facilities and air conditioning. Popular attractions Mermaid Theatre of Nova Scotia and West Hants Historical ...
9.8/10 Exceptional! (7 reviews)
"Great location and nice place. Very cozy and comfortable."

Reviewed on Sep 9, 2026

Gateway to Annapolis Valley | Windsor Studio Suite
Stylish Windsor Suite Near Wineries & Fundy Coast

Stylish Windsor Suite Near Wineries & Fundy Coast

Windsor NS
The price is ¥16,146 per night from Sep 15 to Sep 16
¥16,146
¥26,360 total
Sep 15 - Sep 16
includes taxes & fees
Stay at this apartment in Windsor. Enjoy laundry facilities and air conditioning. Popular attractions Mermaid Theatre of Nova Scotia and West Hants Historical ...
9.6/10 Exceptional! (4 reviews)
"Thoroughly impressed with this property as a whole"

Reviewed on Aug 28, 2026

Stylish Windsor Suite Near Wineries & Fundy Coast
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Gateway to Annapolis Valley | Windsor Studio Suite

Gateway to Annapolis Valley | Windsor Studio Suite

Windsor NS
Stay at this apartment in Windsor. Enjoy laundry facilities and air conditioning. Popular attractions Mermaid Theatre of Nova Scotia and West Hants Historical ...
9.8/10 Exceptional! (7 reviews)
"Great location and nice place. Very cozy and comfortable."

Reviewed on Sep 9, 2026

Gateway to Annapolis Valley | Windsor Studio Suite
Stylish Windsor Suite Near Wineries & Fundy Coast

Stylish Windsor Suite Near Wineries & Fundy Coast

Windsor NS
Stay at this apartment in Windsor. Enjoy laundry facilities and air conditioning. Popular attractions Mermaid Theatre of Nova Scotia and West Hants Historical ...
9.6/10 Exceptional! (4 reviews)
"Thoroughly impressed with this property as a whole"

Reviewed on Aug 28, 2026

Stylish Windsor Suite Near Wineries & Fundy Coast
Micro Boutique Living Wolfville

Micro Boutique Living Wolfville

3.5 out of 5
336 Main Street Wolfville NS
Stay at this apartment in Wolfville. Enjoy free WiFi, parking (surcharge), and daily housekeeping. Our guests praise the convenient parking and the clean rooms ...
Micro Boutique Living Wolfville
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Stay near popular Windsor attractions