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Considering a small town to retire to in 2030-35. Recommendations?

I have a former boomer coworker who sold his house in the east end and just retired in Peterborough. Originally, he wanted to retire in Guelph or Elora, but he said he got a much better bang for his buck east of the city.

Former co-worker or former boomer (how does that work?) ;)

A brother-in-law moved from the city (St. Clair/O'Conner-ish) to just outside of Cambellford. He has a post-retirement (ok, forced downsized) gig which he mostly do online with the odd trip into the city via train.
The bang for the buck depends on where you go. Although anyplace will be cheaper than the city, Prince Edward County has been 'found' and is much pricier that it used to be. As a general statement, I think anything north of the 401 would be cheaper.
 
Nobody ever talks about Kingston. It's probably the nicest sub-200,000 sized city in Ontario. It has an impressive, historic downtown. It's also too far from both Montreal and (far more significantly) Toronto to be a draw for commuters, so you wouldn't have to worry about competing with that annoying demographic. It would be high on my list if I can ever escape this godamn place...
I did a search on Kingston and surrounding area and found some nice homes under $500k. The little town of Verona looks nice, well north of Kingston though.
 
Little towns look nice. But it’s a very different lifestyle from urban centres. Like anything, its not for everyone so you can’t just go by looks.
 
Prince Edward County has been 'found' and is much pricier that it used to be. As a general statement, I think anything north of the 401 would be cheaper.
Prince Edward County has become too hipster like for my taste. The small towns to the west of Ottawa are affordable. Here‘s a nice one in Cobden for under $325 https://www.realtor.ca/real-estate/22988615/24-gould-street-cobden-cobden

A friend of mine just got a job at a feed mill in St. Mary’s, ON. Houses there are affordable, and they have a historic VIA station with daily runs to Toronto.
 
Prince Edward County has become too hipster like for my taste. The small towns to the west of Ottawa are affordable. Here‘s a nice one in Cobden for under $325 https://www.realtor.ca/real-estate/22988615/24-gould-street-cobden-cobden

A friend of mine just got a job at a feed mill in St. Mary’s, ON. Houses there are affordable, and they have a historic VIA station with daily runs to Toronto.

I used to have relatives who lived in The County and it used to be a basic rural economy along with shoreline cottaging. The last time I was down there on the bike it was all boutiques, bistros and wineries. No doubt good for the economy but it sure has driven the prices up. Even in the '80s, I was up for a transfer to the area (didn't happen) and found the housing prices much better north of Belleville (Sterling, etc.); nice rolling countryside. If I had to go east in Ontario I would look at the Gananoque-Brockville area.

At the end of the day, there are lots of good towns provided you can find work, if you still have to.
 
There's a huge difference between a 'nice/pretty' small town and one where aging Admirals can drop anchor while still being able to easily get to doctors, dentists, hospitals etc and be able to walk to buy a pint of milk when his eyes (even with the telescope) no longer allow him to drive. I know people who have moved to small towns or distant suburbs but who later needed to move back to the Big Smoke for reasons of convenience.
Why don't parents live with their kids or in the vicinity? It is easier to cope with life's hardships together.
 
Sometimes I go on the hunt to try to discover quaint towns in Ontario that have a charming, historic downtown with well kept Victorian buildings and vibrant main streets. Last weekend I spent a few days in Niagara Falls (which remains a perplexingly strange city), and on the way back to Toronto decided to swing through a few places I'd never checked out before: Fort Erie, Port Colbourne, and Welland.

Fort Erie: I must have driven a circle around the old downtown, because I didn't see it at all. Can't be very big in that case. Saw lots of generic 50's bungalows. Not a single person walking around anywhere. Very little traffic. Oddly sleepy place. The waterfront park along the lake looked nice and had a great view of the skyline of Buffalo right across, but again, not a soul around on a beautiful Saturday afternoon, which made it feel a bit eerie (pun intended). Unlikely to ever go back.

Port Colbourne: An improvement, with nice parks along the lake, large ships in the canal, and a nice little old downtown area with some activity, but to be honest I was really expecting more. It didn't wow me like some towns. Maybe I missed something. Might go back sometime, but it's not a priority.

Welland: Very underwhelming, to say the least. The downtown area looks economically depressed, with many vacant lots and businesses and neglected buildings (of which, very few were interesting). Frustrating amount of one-way streets. The few people walking around looked shady. Zero vibrancy or tourist appeal - the smattering of existing retail looked like it was straight out of the 70's, which is a bit shocking for a city of its size (50,000+). Major Rust Belt vibes. The tall iron bridge over the canal was the only thing of interest, but since Port Colbourne has a nearly identical one, Welland's is redundant in that sense. Of all the towns and cities I've seen in Ontario, so far only Brantford made a worse impression on me. Definitely never going back, and definitely not a place to retire to (although I'm sure the real estate is affordable)!
 
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Sometimes I go on the hunt to try to discover quaint towns in Ontario that have a charming, historic downtown with well kept Victorian buildings and vibrant main streets. Last weekend I spent a few days in Niagara Falls (which remains a perplexingly strange city), and on the way back to Toronto decided to swing through a few places I'd never checked out before: Fort Erie, Port Colbourne, and Welland.

Fort Erie: I must have driven a circle around the old downtown, because I didn't see it at all. Can't be very big in that case. Saw lots of generic 50's bungalows. Not a single person walking around anywhere. Very little traffic. Oddly sleepy place. The waterfront park along the lake looked nice and had a great view of the skyline of Buffalo right across, but again, not a soul around on a beautiful Saturday afternoon, which made it feel a bit eerie (pun intended). Unlikely to ever go back.

Such as it is................I think you were looking for this:


Ft. Erie is not really a thing.............LOL........

Its comprised of several smaller historic communities that were amalgamated. Ft. Erie and Bridgeburg actually came together in 1930 or thereabouts; but then Crystal Beach and a few other places were consolidated to it in 1970.
Bridgeburg's downtown is on Jarvis Street.

Welland: Very underwhelming, to say the least. The downtown area looks economically depressed, with many vacant lots and businesses and neglected buildings (of which, very few were interesting). Frustrating amount of one-way streets. The few people walking around looked shady. Zero vibrancy or tourist appeal - the smattering of existing retail looked like it was straight out of the 70's, which is a bit shocking for a city of its size (50,000+). Major Rust Belt vibes. The tall iron bridge over the canal was the only thing of interest, but since Port Colbourne has a nearly identical one, Welland's is redundant in that sense. Of all the towns and cities I've seen in Ontario, so far only Brantford made a worse impression on me. Definitely never going back, and definitely not a place to retire to (although I'm sure the real estate is affordable)!

Welland needs to move the Niagara College campus to downtown, its the only real hope!
 
I just got back from a motorcycle tour of Manitoulin Island. I fell in love with the place. I imagine the winters very harsh though.

You're not the first to make that discovery. I don't think the winters are particularly harsh for that latitude (obviously, snowier and colder than Toronto). One site I saw showed the average hi/low for Jan/Feb as -5*C/-10*C, with 35-40cm snowfall/month. I imagine being surrounded by water that doesn't always freeze over (except the North Channel) probably moderates things.

Edit: If you're back up that way, take a turn around St. Joseph's Island, and I know of a great circle trip of a couple of days up that way.

Sometimes I go on the hunt to try to discover quaint towns in Ontario that have a charming, historic downtown with well kept Victorian buildings and vibrant main streets.

Head east along old Hwy 2 and perhaps a side trip to the Perth/Merrickville area. Brockville is my favourite down that way, Gananoque a close second.
 
Perhaps a topic of discussion for the Urban Sprawl thread, but I wouldn't mind a concerted effort from the provincial level to concentrate some of the regional growth into Welland and Port Colborne.

Seems like a St. Catharines, Thorold/Niagara Falls, Welland, Port Colborne corridor would have potential as an urban conglomeration, but currently are not exactly brimming examples of Ontario's vibrancy as per Towered's recent tour.
 
Sometimes I go on the hunt to try to discover quaint towns in Ontario that have a charming, historic downtown with well kept Victorian buildings and vibrant main streets. Last weekend I spent a few days in Niagara Falls (which remains a perplexingly strange city), and on the way back to Toronto decided to swing through a few places I'd never checked out before: Fort Erie, Port Colbourne, and Welland.

Fort Erie: I must have driven a circle around the old downtown, because I didn't see it at all. Can't be very big in that case. Saw lots of generic 50's bungalows. Not a single person walking around anywhere. Very little traffic. Oddly sleepy place. The waterfront park along the lake looked nice and had a great view of the skyline of Buffalo right across, but again, not a soul around on a beautiful Saturday afternoon, which made it feel a bit eerie (pun intended). Unlikely to ever go back.

Port Colbourne: An improvement, with nice parks along the lake, large ships in the canal, and a nice little old downtown area with some activity, but to be honest I was really expecting more. It didn't wow me like some towns. Maybe I missed something. Might go back sometime, but it's not a priority.

Welland: Very underwhelming, to say the least. The downtown area looks economically depressed, with many vacant lots and businesses and neglected buildings (of which, very few were interesting). Frustrating amount of one-way streets. The few people walking around looked shady. Zero vibrancy or tourist appeal - the smattering of existing retail looked like it was straight out of the 70's, which is a bit shocking for a city of its size (50,000+). Major Rust Belt vibes. The tall iron bridge over the canal was the only thing of interest, but since Port Colbourne has a nearly identical one, Welland's is redundant in that sense. Of all the towns and cities I've seen in Ontario, so far only Brantford made a worse impression on me. Definitely never going back, and definitely not a place to retire to (although I'm sure the real estate is affordable)!
I grew up in Niagara. It definitely is rust belt. Of the three, I think Port Colborne is the most pleasant, but it doesn't have a whole lot of employment opportunities. There are definitely rough parts of town and the downtown retail is underwhelming. Housing prices are really climbing there, though. $500k doesn't go very far.
 

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