Does Winchester have a hipster family vibe? (Richmond, Arlington: real estate, hotel)

[Rebevkah]

My husband and I dream of buying a big old house in a downtown area with good schools where we can walk or ride our bikes regularly. I graduated from the Conservatory at Shenandoah University in 2003 and haven't been back to visit Winchester much since that time. We currently live in Henrico County just outside of Richmond City and my husband who works from home, recently drove through Winchester and was perplexed as to why I didn't mention what an idealistic town it is and why I had never wanted to move back.
In all honesty, I imagine my perspective of Winchester as a twenty year old theatre student would be quite different than my current perspective as a thirty five stay at home Mom of a four and one year old. Like so many parts of our youth, I dismissed Winchester as being small and boring so I never mentioned it. But now he has me thinking, " could we move to Winchester?" I loved riding my bike all over town and having coffee at The Daily Grind and having my first legal drink at Sweet Carolines! There are so many reasons why I could imagine growing up there might be magical.
So...to get to the point:
1) How has Winchester changed over the past fifteen years?
2) Has it become more culturally diverse?
3) I realize some of you may loathe this statement so forgive me in advance but it's the most direct way of asking: Is there a hipster family scene happening in Winchester? I'm talking liberals in their 30's who may be slightly more alternative- organic eating, nerd glasses wearing, Bernie Sanders lovers. I may or may not have just described myself. This not a political post but I am just curious about the feel of the town now as I'm sure it is not only different than I remember it and possibly changed since I lived there.
4) Are there young families who live downtown?

I loved going to SU and had some beautiful experiences in Winchester City, just seeking some advice.

[spencgr]

Originally Posted by Rebevkah

. I may or may not have just described myself.

Ah....I'm pretty sure you definitely just described yourself.


There are a few people on this forum who are more intimately familiar with Winchester. By and large, it is more conservative; but that doesn't mean a hipster contingency doesn't exist.

[Rebevkah]

Thank you! I absolutely did describe myself! I was being sarcastic when I wrote that! We are currently looking at (lusting over) homes in downtown Winchester on Zillow. It's a gorgeous town!

In all honesty, I prefer a blend of liberals and conservative because it helps us all grow and think! I was just curious if there was a little sub culture that we could connect with as well.

[boyd888]

Not really. I'd consider to be much more conservative and rural. I'm sure there are liberals there, but what you are looking for is definitely more the Arlington/Alexandria area than Winchester.

[Rebevkah]

Originally Posted by boyd888

Not really. I'd consider to be much more conservative and rural. I'm sure there are liberals there, but what you are looking for is definitely more the Arlington/Alexandria area than Winchester.

Although I love Alexandria, real estate is out of our price range. We are looking to spend 4 to 550k at most which is why Winchester seems appealing- we can afford an awesome old home in a great school district. We love Richmond City but the schools just aren't there yet. We currently live in an excellent school district but crave a more village type feel like Alexandria or Fredericksburg or perhaps Winchester. Maybe we are asking too much which is entirely possible

[Ffxdata]

I would say that those people do live there. There is a delightful little shop on the main drag called TinTop which is as twee as it gets. Hand carved wood baby toys? Check. Hand made screen printed shirts? Check. The area has an Alamo Drafthouae imported straight from Austin.

The locals though seem to be more rural types. There were plenty of Trump signs. I've spent time there in bars and restaurants and considered buying a home but much of the downtown area is run down.

Personally, I'd go for Culpeper if driving isn't a concern. That way you have DC or Charlottesville to go to.

[bobamike]

I live in Winchester. Overall it's conservative, which is why I like it. But there is a population of hipsters with beards, tight jeans, and thick glasses if that is what you are looking for. There is an alternative lifestyle coffee house that has become popular lately. Sweet Caroline's is gone, replaced with a burger/beer place that is overrun with those types

Downtown is not run down at all, it was redone just a few years back. They are currently working on building a large upscale hotel/conference center downtown.

I think it's a great place to raise a family. Good schools. Not too pricey, lots to do, and close to DC.

[Old Guard]

Originally Posted by Rebevkah

In all honesty, I prefer a blend of liberals and conservative because it helps us all grow and think! I was just curious if there was a little sub culture that we could connect with as well.

Not to insult you but to me this is a very odd thought when purchasing a house. I am not even sure it would cross my mind.

But I think you would be better served upping your budget and looking at Del Ray and Arlandria.

Of course I do not know your commute(s) so this may not be possible.

[NOVA_guy]

Lol, um no

[Hal Roach]

If there is any vibe it is from mariachi band. I used to live near the Mexican border and would cross to buy avacadoes at seven for a dollar and bet the horses. It was amazing how many of the Mexicans mentioned "Ween-chester, when I told them my familia was from Berheenia. 500k for a home there? I would actually rather live in Mexico....at least you wouldn't be surrounded by illegals.