Rhinebeck NY. There was another thread about this area that described it as nice

Rockport, MA
Falmouth and woods hole, MA. It's cape cod but has a good year round population
South Dartmouth, MA
The Berkshire towns other posters have mentioned ....

Providence

Anonymous wrote:Annapolis.

Not hipster. More like a cross between tourist and redneck.

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:I was going to say Lenox or Northhampton MA. Or there's a place in Vermont...I always get the towns in Vermont mixed up, though.
But real hipster places definitely don't have Chipotle or Starbucks. They have fancy coffee places named after a guy that lives there that bakes vegan scones and grinds and roasts his own coffee on site. They wouldn't be caught dead drinking starbucks.
If you just want to make sure you can eat a taco and a latte, that's easy.

Not a hipster myself, but this is definitely my impression.

It sounds to me that this person really wants retiree quaint over hipster quaint. Wilmington, NC is a good bet, but I would also recommend CT. There are a number of cute towns on or the near the water like Guilford that have a green with cute shops around it. But you can still drive a mile or two and get your Dunking Donuts, Chipolte, Starbucks or whatever.

In that case, maybe somewhere like Mystic? I think you can go on the train.

Not on the water, but Carboro NC and chapel hill NC.

Richmond VA is not a small town, but very hipster and on the James River. Norfolk VA is also not small, has crime, but is trying to reinvent a hipster downtown and is on the water.

Anonymous wrote:Annapolis.

Lol. This must be a joke.

Most of the places people have been posting seem more hippie than hipster to me. (Ex: Asheville) I don't watch the shows op referred to so I'm not sure what he/she is looking for.

The best suggestion I've seen is richmond. Maybe Savannah. Most places with strong art schools have a lot of hipsters.

Anonymous wrote:

Anonymous wrote:It sounds like maybe you want nice with a patina of quaint but not really hipster?

You know I've never thought of it like that - perhaps that is what I'm looking for. Not sure if there is a word for that though.

David Brooks wrote a book about this demographic and called it bourgeois bohemian (BOBO). It's not hipster by a long chalk.

Anonymous wrote:

Anonymous wrote:I was going to say Lenox or Northhampton MA. Or there's a place in Vermont...I always get the towns in Vermont mixed up, though.
But real hipster places definitely don't have Chipotle or Starbucks. They have fancy coffee places named after a guy that lives there that bakes vegan scones and grinds and roasts his own coffee on site. They wouldn't be caught dead drinking starbucks.
If you just want to make sure you can eat a taco and a latte, that's easy.

Not a hipster myself, but this is definitely my impression.

It sounds to me that this person really wants retiree quaint over hipster quaint. Wilmington, NC is a good bet, but I would also recommend CT. There are a number of cute towns on or the near the water like Guilford that have a green with cute shops around it. But you can still drive a mile or two and get your Dunking Donuts, Chipolte, Starbucks or whatever.

Anonymous wrote:I was going to say Lenox or Northhampton MA. Or there's a place in Vermont...I always get the towns in Vermont mixed up, though.
But real hipster places definitely don't have Chipotle or Starbucks. They have fancy coffee places named after a guy that lives there that bakes vegan scones and grinds and roasts his own coffee on site. They wouldn't be caught dead drinking starbucks.
If you just want to make sure you can eat a taco and a latte, that's easy.

Not a hipster myself, but this is definitely my impression.

Asheville. But it's more crunchy than hipster. I don't get the need to be near a Chipotle.

Anonymous wrote:It sounds like maybe you want nice with a patina of quaint but not really hipster?

You know I've never thought of it like that - perhaps that is what I'm looking for. Not sure if there is a word for that though.

Anonymous wrote:I would caution not to stray too far from the beaten path. You'd be surprised how 'Southern' most of NC really is... definitely no hipster vibe there.

Thanks for the warning.

Anonymous wrote:I was going to say Lenox or Northhampton MA. Or there's a place in Vermont...I always get the towns in Vermont mixed up, though.
But real hipster places definitely don't have Chipotle or Starbucks. They have fancy coffee places named after a guy that lives there that bakes vegan scones and grinds and roasts his own coffee on site. They wouldn't be caught dead drinking starbucks.
If you just want to make sure you can eat a taco and a latte, that's easy.

Thanks for the tips! I like the simple things in life and since this will be a working vacation, having my staples around will help me work. So yes, not ardent hipster or fancy restaurants every day, just the occasional dinner.

Anonymous wrote:I feel like this is a bet and the OP wants DCUM to guess the right city. Like she is arguing with a friend that Portland is totally not hipster but if DCUM says it is...

Just looking to outsource some vacation help, these tips have been gold!

---

Thank you from the OP! To address some common notes, this is a business vacation and I will be working from wherever I go. Since it'll be 1-2 weeks I want to feel comfortable and be able to grocery shop / eat at my local haunts as well as exploring more interesting dining options. Plus I'm cheap when it comes to eating out.

Anonymous wrote:I was going to say Lenox or Northhampton MA. Or there's a place in Vermont...I always get the towns in Vermont mixed up, though.
But real hipster places definitely don't have Chipotle or Starbucks. They have fancy coffee places named after a guy that lives there that bakes vegan scones and grinds and roasts his own coffee on site. They wouldn't be caught dead drinking starbucks.
If you just want to make sure you can eat a taco and a latte, that's easy.

x 100

Anonymous wrote:Annapolis.

What? Annapolis skews preppy, not hipster

Northampton, MA

Also Richmond, VA (RVA) is only a 2 hour drive, has awesome restaurants/breweries and the James River has great kayaking and swimming.

Also, RVA folk are Southern boho yoga chicks or lumbersexual dudes- I've been trying to convince my husband that we should move there- the only drawback is that schools are pretty bad in the city.