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

Admiral Beez

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After almost 22 years living in downtown east, I am beginning to think of retirement in the next fifteen years, and maybe renting out my current home and living somewhere else. Somewhere without the crazies, beggars, park encampments, graffiti and the other signs of a municipality struggling with poverty and neglect. By 2030 or 2035 I expect Toronto's downtown east will be equally better (Regent Park development, more gentrification, better shops, etc...) and worse (bankrupt city, homeless, addiction and mentally ill issues, etc.).

I’d like to find an Ontario town with an historic Main Street with walkable retail. Nor do I want a Costco or Walmart nearby that threatens the town. I lived in Fredericton, New Brunswick for three years in the early 2000s and had to drive everywhere for food, etc., so want something walkable, just like I have in Cabbagetown now. Towns like these are of mind, https://www.narcity.com/travel/ca/o...o-when-you-want-to-get-away-from-the-big-city and https://www.tvo.org/programs/main-street-ontario Of course small towns have addiction issues, especially opiates, and often far worse on a per capita than Toronto's, but it's mostly behind closed doors and out of mind, rather than camped in my local park.

I drive small town Ontario for work and often stop in small towns for a bite, such as New Hamburg, Warkworth or Fordwich and often fall for the quaint, old world look of the places. What small towns do you like and recommend?
 

AlbertC

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For retirement purposes, the Muskoka towns like Bracebridge, Gravenhurst and Huntsville are the typical ones that come to mind. Some of my retired clients often refer to the area as "God's country".

As you head towards Georgian Bay there's also Midland and Penetanguishene. Further west is Wasaga Beach and Collingwood but you'll be getting a lot of tourists during summer and winter depending on what activities people are going for.

Consider Tobermory or other communities along the Bruce Peninsula if you want to get even further away. There's frequent summer visitors as camping and the Grotto are popular attractions but overall there's a decent balance between nature, tranquility, and small town charm. Or places like Kincardine or Goderich along Lake Huron.

Other options throughout the province, there's the Belleville-Quinte-Prince Edward County area as you head eastward closer to Kingston. I've also known someone younger who lives in Port Hope and travels to Toronto for work.

While in terms of smaller cities in general maybe consider Guelph, Cambridge, Peterborough or quaint towns like Elora, Paris and Fenelon Falls.
 

Jonny5

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After almost 22 years living in downtown east, I am beginning to think of retirement in the next fifteen years, and maybe renting out my current home and living somewhere else. Somewhere without the crazies, beggars, park encampments, graffiti and the other signs of a municipality struggling with poverty and neglect. By 2030 or 2035 I expect Toronto's downtown east will be equally better (Regent Park development, more gentrification, better shops, etc...) and worse (bankrupt city, homeless, addiction and mentally ill issues, etc.).

I’d like to find an Ontario town with an historic Main Street with walkable retail. Nor do I want a Costco or Walmart nearby that threatens the town. I lived in Fredericton, New Brunswick for three years in the early 2000s and had to drive everywhere for food, etc., so want something walkable, just like I have in Cabbagetown now. Towns like these are of mind, https://www.narcity.com/travel/ca/o...o-when-you-want-to-get-away-from-the-big-city and https://www.tvo.org/programs/main-street-ontario Of course small towns have addiction issues, especially opiates, and often far worse on a per capita than Toronto's, but it's mostly behind closed doors and out of mind, rather than camped in my local park.

I drive small town Ontario for work and often stop in small towns for a bite, such as New Hamburg, Warkworth or Fordwich and often fall for the quaint, old world look of the places. What small towns do you like and recommend?
Well a lot of what you are looking for comes at a high price because many people have already done it or are planning to do it. Premium towns along the 401 like Coburg will set you back big bucks for a house now.
There really aren't many "small" towns that have a historic Main Street with a lot of retail left because there's Wal-Marts everywhere. Even if there isn't one in town, people will drive to one that's 30 minutes away in another town. The touristy places are an exception: Stratford, NOTL, etc..
But maybe Owen Sound would fit? It's got the retail, it's scenic, and it is a "regional centre" so it has the big local hospital, etc. and it still l seems to be far enough away from the beaten path that it hasn't had a housing boom from retired people leaving the city yet.

Or are you looking for somewhere even smaller?
 
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Northern Light

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I think I might put in for Alliston.

Its still got a fairly intact main street, some nice old homes; there is big box retail further out, but also a Zehr's that's only a block removed from the main street; so lots of nice walking choices.

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Towered

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After almost 22 years living in downtown east, I am beginning to think of retirement in the next fifteen years, and maybe renting out my current home and living somewhere else. Somewhere without the crazies, beggars, park encampments, graffiti and the other signs of a municipality struggling with poverty and neglect. By 2030 or 2035 I expect Toronto's downtown east will be equally better (Regent Park development, more gentrification, better shops, etc...) and worse (bankrupt city, homeless, addiction and mentally ill issues, etc.).

I’d like to find an Ontario town with an historic Main Street with walkable retail. Nor do I want a Costco or Walmart nearby that threatens the town. I lived in Fredericton, New Brunswick for three years in the early 2000s and had to drive everywhere for food, etc., so want something walkable, just like I have in Cabbagetown now. Towns like these are of mind, https://www.narcity.com/travel/ca/o...o-when-you-want-to-get-away-from-the-big-city and https://www.tvo.org/programs/main-street-ontario Of course small towns have addiction issues, especially opiates, and often far worse on a per capita than Toronto's, but it's mostly behind closed doors and out of mind, rather than camped in my local park.

I drive small town Ontario for work and often stop in small towns for a bite, such as New Hamburg, Warkworth or Fordwich and often fall for the quaint, old world look of the places. What small towns do you like and recommend?
How small are we talking?

Orillia is quite charming, and I don't think it's too beset by awful big box retail yet.
 

TorPronto

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Downtown Guelph is complete as in you could get everything done without leaving to go out to Walmart/Costco etc (but still has those options). In downtown Guelph, you can walk to the grocery store, all banks, the post office, brewery, cafes, restaurants, dry cleaning, tailor, clothing stores, etc. You can walk to the train station to go downtown or catch the VIA for something further out. Prices are already inflated though.
London is cheaper but I can't comment on their downtown.
Windsor's downtown was surprisingly nice the one time I visited a few years back.
 

DSC

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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.
 

Admiral Beez

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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.
That's one reason towns along the Sarnia/Windsor-Cornwall VIA line have appeal, but they are pricey.



Glencoe, near Windsor is on the tracks.
 
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lenaitch

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An interesting post and some interesting responses. Much depends on the questions of 'how small' and 'how far away'. I've lived in a few r-e-a-l-l-y small and remote places and enjoyed everyone one of them for varying reasons but, as DSC mentions, as you get older, your priorities change. Finding health care in smaller communities can be a challenge, and access to some specialties can be more difficult. I know of people who have moved into towns from more rural areas, like their winterized cottage, because 'back of beyond' becomes more difficult as you age, and the vast difference between life in February as opposed to the summer as they knew it was quite different. I currently live in Huronia but out of town so walkablility isn't a thing for us, but a few random thoughts for what they are worth:

- If the catchment area is big enough, it will have big box stores, and if it has big box stores, 'downtowns' struggle, to varying degrees of success.
- Many places within x distance to the GTA will be impacted by tourism, retirement and distance commuting to varying degrees, including housing prices and traffic. Many older downtowns simply weren't built to handle the seasonal hoardes.
- Look at taxes as well as price. Many of these places no longer have a commercial base so residential bears much of the load.
- Orillia, Midland, Penetanguishene are decent. Like many small towns, the drug problem isn't as hidden as you think.
- I lived in Muskoka and always felt it had it's head too far up its own butt. Obviously, anything on water will be off the dial - town lots still pricey but not so much. Taxes are high especially Huntsville (which probably also has the highest housing prices. I've always liked Parry Sound. Decent downtown and prides itself in not being Muskoka. A little more rough and ready being part of a northern district.
- Wasaga Beach has to be the least walkable place on the planet.
- Collingwood, Thornbury and Meaford are quite nice, but have become pricey.
- Although I've occassionally worked there, I don't know much about western Ontario. S/W Ontario is, to me, just plain too flat. I like the looks of Goderich.
- A B-i-L moved to Campbellford from downtown Toronto and likes it. In eastern Ontario, prices north of the 401 are probably cheaper than along the lakeshore. Prince Edward County is nice but has become quite expensive.
- If it were up to me, I would move to the Gananoque-Brockville area. Brockville has quite a nice downtown. Most if not all of the box stores are north of the 401. I think it's far enough out to not be too badly impacted by the GTA.

Actually, if I had my druthers I'd already be somewhere in the Annapolis Valley in NS but you've set your limit on Ontario.

Good on your for planning ahead, but keep in mind many of these places are a 'whole nudder world' in the winter.
 

Towered

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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...
 

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