Asheville's Architecture: From Vanderbilt Excess to That Pink Dome Thing
Three days of geeking out over buildings that survived because we were too broke to tear them down
Dylan's Real Voice
The Hook:
"I literally stop mid-run on the RAD Greenway to stare at the S&W Building's Art Deco details. Like, every single time."
Personal Story:
When I moved here from Boston, I expected mountains and hippies. What I got was this insane outdoor architecture museum where America's richest man built a 250-room 'cottage' and some Italian guy made a dome without steel reinforcement just to flex. Now I'm that person making friends wait while I photograph cornices.
Why This Matters:
Look, two things can be true at once: Asheville's a small mountain town AND it has architecture that rivals major cities. Most of it survived because after the Depression, we were too broke to tear anything down. Financial disaster led to architectural treasure, and now I get to run past Art Deco masterpieces on my morning route.
☕ I've had probably 15 cortados at Battery Park Book Exchange alone while staring at the Grove Arcade's details
Your Weekend Schedule
Downtown Icons & Art Deco Dreams
Dylan's routine: If you're anything like me, you're up at 5:30 for a run. Hit the Urban Trail early - it's 1.7 miles of sculptures and architecture without tourists.
Rowan Coffee
✓ Dylan's been hereFuel up with the best cortado in town
Dylan says:
"Their new West Asheville spot is gorgeous. I'm here literally once a week minimum. Get the cortado - trust me, I've tried them all."
Frequency: Weekly, sometimes twice
Grove Arcade
✓ Dylan's been hereTudor and Gothic Revival marketplace from 1929
Dylan says:
"I bring every out-of-town client here. The government seized it for WWII, then it sat empty forever. Now it's where I pretend I'm in a Wes Anderson film while getting coffee."
Frequency: 50+ times with clients
Insider Tip: Battery Park Book Exchange in the basement - vintage books and champagne. It's a whole vibe.
S&W Market
✓ Dylan's been herePost-Helene: modifiedArt Deco cafeteria building turned food hall
Dylan says:
"The ceiling alone is worth the visit. I literally bring clients here just for the wow factor. It's giving Great Gatsby meets mountain town."
Frequency: Monthly
Insider Tip: Sit in the main hall to appreciate the restored details. Check what's actually open post-Helene.
Basilica of St. Lawrence
✓ Dylan's been hereSpanish Renaissance Revival with Guastavino dome
Dylan says:
"That dome? No steel reinforcement. Just tiles and faith. Rafael Guastavino basically said 'hold my beer' to physics. Largest freestanding elliptical dome in North America."
Frequency: Shown to dozens of visitors
Insider Tip: The 11am Sunday mass has incredible acoustics if you want the full experience
City Building (City Hall)
✓ Dylan's been hereDouglas Ellington's Art Deco octagonal masterpiece
Dylan says:
"Ellington went absolutely nuts with this building. Pink and green tiles, octagonal shape, ziggurat roof. It's like if Miami Beach Art Deco had a baby with a Mayan temple."
Insider Tip: The interior is even wilder than the exterior. Just walk in like you belong.
All Day Darling
✓ Dylan's been hereDinner in a mid-century modern gem
Dylan says:
"This is where I take clients for meetings. The interior is as photogenic as the food. Mid-century modern everything."
Frequency: Weekly for client meetings
Insider Tip: Sit at the bar to watch the open kitchen - it's dinner theater
Night Architecture Walk
✓ Dylan's been hereSelf-guided tour of illuminated buildings
Dylan says:
"Download the Asheville Architecture Trail app (actually useful). Hit Jackson Building (Gothic Revival), First Baptist (that pink dome!), and the Flatiron."
Insider Tip: The buildings look completely different lit up at night. Bring a real camera.
Gilded Age Excess & Industrial Revival
Dylan's routine: Long run day for me - I'd hit Bent Creek early. But for you, fuel up and prepare for Vanderbilt madness.
Biltmore Estate
✓ Dylan's been hereAmerica's largest private home - 250 rooms of Gilded Age insanity
Dylan says:
"Look, it's touristy and expensive but holy shit, Vanderbilt really said 'I'm going to build Downton Abbey but make it Appalachian.' The gardens were designed by Frederick Law Olmsted (Central Park guy). It's absolutely bonkers."
Frequency: Every time family visits
Insider Tip: Book the first entry to avoid crowds. The gardens are actually more impressive than the house.
Late lunch break
✓ Dylan's been hereRecover from Biltmore overwhelm
Dylan says:
"You need a break after Biltmore. Trust me."
Insider Tip: Village Social in Biltmore Village if you're not ready to leave the area
River Arts District
✓ Dylan's been herePost-Helene: modifiedIndustrial warehouses turned artist studios
Dylan says:
"This is where I run every morning. The contrast between the industrial bones and the art is wild. Post-Helene, it's different but recovering."
Frequency: Literally every morning for runs
Insider Tip: Second Saturdays mean open studios. Otherwise, Foundation Studios has the best variety.
Highland Brewing
✓ Dylan's been hereSunset beers on the rooftop
Dylan says:
"This is my spot. Tuesday night volleyball, Saturday leagues. The rooftop has panoramic views of the city and mountains. You can see all the architecture you visited from up here."
Frequency: 2-3 times per week for volleyball
Insider Tip: Tuesday nights the volleyball crowd takes over. It's basically a gay sports bar without calling itself that.
Sacred Spaces & Neighborhood Character
Dylan's routine: Sunday is recovery run day - easy pace through Montford to look at houses
Montford Historic District
✓ Dylan's been hereSelf-guided tour through 600+ historic homes
Dylan says:
"I show houses here all the time. It's where Asheville's elite built their 'modest' homes compared to Biltmore. Every architectural style from 1890-1930."
Frequency: Weekly for showings
Insider Tip: Riverside Cemetery nearby has gorgeous monuments and mountain views. Thomas Wolfe and O. Henry are buried there.
Brunch break
✓ Dylan's been hereFuel up in Montford
Dylan says:
"There are spots in Montford but honestly, I usually head back toward downtown"
Insider Tip: Check what's open - this area changes frequently
Thomas Wolfe Memorial
✓ Dylan's been hereTour the author's childhood home - Queen Anne style
Dylan says:
"The house is called 'Old Kentucky Home' in his novel. It's a preserved boarding house that shows how people actually lived here in the 1920s."
Insider Tip: The visitor center has great context about 1920s Asheville
Cathedral of All Souls
✓ Dylan's been herePink sandstone Gothic Revival
Dylan says:
"Vanderbilt built this for the village. It looks like it was airlifted from England. Pink sandstone in the mountains - only in Asheville."
Insider Tip: The Biltmore Village historic cottages around it are worth the walk
Dylan's Must-Do List
- S&W Building ceiling - seriously, look up
- Basilica dome - no steel, just vibes
- Grove Arcade basement - books and champagne
- Highland Brewing rooftop at sunset - see everything from above
- Night photography of City Hall - it's absolutely wild lit up
- Actually download the Architecture Trail app - not tourist BS
Reality Check
- Biltmore is expensive but worth it once
- Some RAD studios are still recovering from Helene
- Parking downtown is a pain - walk or park once and leave it
- Buildings are more impressive inside - just walk in
- Check what's actually open before you go
- The Urban Trail is actually good - do it early before tourists
Where to Stay
Getting Around
- • Walk downtown
- • Drive to Biltmore and RAD
- • Download the Urban Trail app
Photo Ops
Want This Itinerary + Updates?
Get this itinerary as a PDF, plus monthly updates on what's new in Asheville and insider tips I don't share publicly.
Get the Gay Asheville Guide
Real talk about LGBTQ+ life, neighborhoods, and making friends in Asheville.
No spam, just insider tips from a local. Unsubscribe anytime.
Ready to Make Asheville Home?
Loved this itinerary? Imagine living here. I help LGBTQ+ folks and allies find their perfect Asheville home every day. No pressure, just honest advice from someone who's been in your shoes.
Or just have questions? Reach out anytime - I love talking about Asheville.
You Might Also Like
Finding Your Chosen Family in the Blue Ridge
A queer-centered weekend celebrating Asheville's LGBTQ+ community
View ItineraryEat Pray Love But Just the Eat Part
Three days of culinary excellence
View ItineraryChasing the Almost Famous Vibe
Three days of venues and vinyl
View Itinerary