History is woven into the streets, buildings, and shorelines of Barrie and Simcoe County. Whether you’re into military tales, historical architecture, or Indigenous heritage, this region has lots of attractions and stories to tell ... if you know where to look.
Here’s your go-to list of must-see sites, hidden gems, and cultural stops that bring the past to life.
RELATED: Your guide to Simcoe County’s best museums ...
Barrie's News Delivered To Your Inbox
By submitting this form, you are consenting to receive marketing emails from: Central Ontario Broadcasting, 431 Huronia Rd, Barrie, Ontario, CA, https://www.cobroadcasting.com. You can revoke your consent to receive emails at any time by using the SafeUnsubscribe® link, found at the bottom of every email. Emails are serviced by Constant Contact
1. Downtown Barrie’s Historic Core
It’s easy to stroll through downtown Barrie without realizing you’re surrounded by history. But look closer — the city’s waterfront core is home to preserved architecture and stories from the 1800s.
Don’t miss:
- The Five Points intersection, which was once a trading post area and now a hub of 19th-century architecture
- The MacLaren Art Centre housed in a former Carnegie library
- Historical plaques and walking tours that spotlight key moments in Barrie’s development — from its military roots to the Great Fire of 1871
- Close proximity to the Nine Mile Portage trail — once a key trade route
Pro tip: Grab a coffee and stroll along Dunlop Street while keeping an eye out for hidden details inside and outside each building.
2. Historic Fort Willow – Springwater Township
Step into one of Simcoe County’s most important War of 1812 sites. Fort Willow served as a crucial military supply depot along the Nine Mile Portage — a shortcut between Lake Simcoe and Georgian Bay. The portage was critical for moving troops and goods.
Today, Fort Willow’s reconstructed buildings and detailed signage bring that strategic history to life. The site also hosts lively reenactments and special events that engage both history buffs and families alike, making it a perfect interactive stop.
Things to check out:
- Reconstructed military buildings
- Interpretive signage explaining the portage system
- Annual reenactments and special events
Best for: Fans of military history, explorers, and families with curious kids.
3. Nine Mile Portage Trail – Simcoe County
The Nine Mile Portage isn’t just a trail — it’s a historic artery that connected Lake Simcoe with Georgian Bay. Used for centuries by Indigenous peoples and later by European settlers and military, it played a vital role in trade, travel, and defense.
Today, you can hike portions of the trail and imagine the voyageurs, soldiers, and traders who carried goods and stories along this route. Interpretive signs help trace the path’s historical importance.
Why it’s a must-see:
- Key transportation route in Simcoe County’s early history
- Used by Indigenous communities and during the War of 1812
- Outdoor hiking opportunity with educational signage
Bonus: Nine Mile Portage connects to Fort Willow and other historic sites
4. St. James On The Lines Cemetery – Penetanguishene
If you believe every headstone tells a story, this is the place to visit. Established in the early 1800s, St. James-on-the-Lines is one of Ontario’s oldest Anglican cemeteries and is tied directly to Penetanguishene’s historic naval and military roots.
Many of the graves belong to British officers, early settlers, and Indigenous allies. The site is quiet, solemn, and rich with symbolic carvings and hand-chiseled epitaphs. It’s a reminder that local history isn’t just in books — it’s right beneath your feet.
Why it’s a must-see:
- Resting place of early settlers and military figures
- Unique 19th-century grave markers and carvings
- Close to Discovery Harbour and downtown Penetanguishene
Bonus: Guided tours available through local historical societies
5. Mnjikaning Fish Weirs – Orillia
One of the most overlooked historic sites in Ontario also happens to be one of its oldest. The Mnjikaning Fish Weirs were used by Indigenous communities more than 5,000 years ago to catch fish where Lake Simcoe narrows into Lake Couchiching.
Today, while the original wooden stakes lie submerged, their story is told through interpretive signs and Indigenous-led programming. The site reminds visitors that long before roads and railways, this region thrived with knowledge, sustainability, and community.
Why it’s a must-see:
- One of the oldest human-made fishing structures in North America
- Located at a culturally and ecologically rich waterway
- Offers insight into Anishinaabe history and innovation
6. Oro African Methodist Episcopal Church – Oro-Medonte Township
Oro Church stands as a beautiful example of 19th-century religious architecture with deep roots in the local community. Built by early settlers, this historic church has witnessed generations of worship, celebrations, and community gatherings.
The church grounds and nearby cemetery tell stories of the township’s pioneers, while the building itself offers a glimpse into the craftsmanship and values of the era.
Why it’s a must-see:
- Architecturally significant 19th-century church building
- Cemetery with graves of early Oro settlers
- Represents community life and faith in early Simcoe County
RELATED: The History Behind The Oro African Methodist Episcopal Church ...
7. Jury Lands Foundation – Alliston
The Jury Lands Foundation is dedicated to preserving and revitalizing a significant piece of Ontario's history.
Located in Alliston, the site encompasses the former Ontario Boys Training School, established in 1925. It was later known as Camp 30 during World War II when it served as a prisoner-of-war camp for high-ranking German officers.
This unique blend of educational and military history offers a compelling narrative of the region's past.
Why it’s a must-see:
- Unique history as both a boys’ training school and WWII POW camp
- Early 20th-century buildings with interesting architecture
- Tours and events that bring local history to life
- Plans to turn the site into a community park
4. Coldwater Mill – Coldwater
Originally built in the 1830s, this historic grist mill was the centre of life in the early Coldwater settlement. It has been restored and now functions as a community hub, but retains its original structure and riverside charm.
Why it matters:
- Early settler industry preserved in original location
- Part of Coldwater’s roots as a mill town
- Scenic location that still draws visitors
Pro tip: Looking for a little more history to fill your day? Swing by the Coldwater Canadiana Heritage Museum just outside of town on Highway 12.
Honourable mentions
Stayner’s Station Park: Look for remnants of the railway era that helped shape this small town.
Cookstown Antique Market: Not exactly a museum, but packed with items that tell stories of rural Ontario’s past. Use Google Lens to take pictures of unique and interesting items to see if you can find their backstory.
Nottawasaga Lighthouse (Wasaga Beach): One of the oldest lighthouses on the Great Lakes, offering history of maritime navigation and local shipwrecks.
Ramara Pioneer Village (Ramara Township): A small heritage village with restored buildings showcasing pioneer life in rural Ontario.
Tiny Township Heritage Trail (Tiny Township): Features several historic buildings and markers telling the story of the township’s early settlers.
Penetanguishene Naval and Military Museum: Located near Discovery Harbour, it focuses on Penetanguishene’s important naval history and colonial military past.
Shear Park (Site of the Old Barrie Jail): While the original jail was torn down, this park near the courthouse marks the site of Barrie’s first jail and gallows. The area played a central role in 19th-century justice and law enforcement.
Allandale Station – Barrie: This restored 1905 railway station is a gem of Edwardian architecture and was once a bustling hub connecting Barrie to Toronto and northern Ontario. It's now part of the GO Transit system but retains its historical façade and significance.
Simcoe County was made for history lovers
Simcoe County isn’t just lakes and trails — it’s packed with opportunities to time travel. Whether you’re a casual history fan or a full-on buff, there’s no shortage of spots that dig into the roots of this region.
Pack your curiosity, lace up your walking shoes, and bring your camera — Simcoe County’s past is ready to explore.
