Stay in Chapel Hill, at the Carolina Inn if you can afford it. If you can't, there are several nice older places on Highway 54 (Raleigh Road) just out of town across 15/501.

Eat at Allen and Son Barbecue on Highway 86 north of town (funky but absolutely classic) or Crooks Corner on West Franklin, where New Southern Cuisine was practically invented. Without Crooks, places like Comfort in Richmond would never have happened.

Go back to the center of town and walk down Franklin Street and through the historic parts of the University of North Carolina in the dusk. Maybe eat an ice cream.

Eat breakfast at the Carolina Coffee Shop on Franklin Street right in the middle of things or at Momma Dips on West Rosemary. There forever.

Go ahead, make me jealous!

Chapel Hill might be a little farther than we'd like to drive. Any one else have suggestions?

Winston and Greensboro are farther west than Chapel Hill. It's only about 140 miles to Chapel Hill from Richmond which, on the interstate, would take you about 2.5 hours. Chapel Hill would be a great place for an overnight stop. Ackslander gave you great recs.

It's abput 3 1/2 hours from Asheville to Chapel Hill.

I'm actually looking for something on the way back from Asheville, so am looking for something closer to 2.5 hours from Asheville, not Richmond.

Thanks

Well, to answer your first question, of course Winston and Greensboro are "safe".
Winston is a nice smaller town. It has some interesting historic areas. Old Salem is pleasant. Go to the Winkler Bakery. Has good food, and isn't so spread out as maybe Greensboro is.
.

Winston Salem was very nice. Liked the Old Salem area. The Winkler Bakery was so small and crowded we could not eat there. Not too many seats. Was a busy weekend though.
Love Chapel Hill also. Carolina Inn while pricey, is very nice. Lot depends on what you are looking to do.

Don't eat IN the bakery. My favorite memory in my mind is going in the bakery, buying some bread and our 3 kids sitting on the high cobblestone curb tearing off pieces to eat.
Buy one of their famous Moravian sugar cakes for breakfast.

Well, I'm going to recommend something completely different. I'm suggesting you try one of the prettiest valleys I know anywhere and a stay at the Mast Farm Inn - http://www.themastfarminn.com/lodging/

It's not halfway between the two and not really on the way - but Richmond is still less than a 6 hour drive away. Valle Crucis is magical, the inn is wonderful and their food is fabulous. If you want another place to stay, check out Banner Elk or Boone NC nearby. I'd much rather stay in that area and then get back on the road "home".

Be sure to check out the original Mast General Store when you are there - http://www.mastgeneralstore.com/Communities/mast/index.cfm/original-mast-general-store/

The line was so long in the bakery a couple of Saturday's ago and it was hot. Looked neat though. Very tight in there. My son wanted Ice Cream also.

Winston Salem is full of great options. Definitely a stop in Old Salem (www.oldsalem.org) is in order. It is an exceptional historical refurbishment (most of the buildings are original). You might want to overnight at the Zeverly Inn or the Brookstown Inn, both of which are charming. As to eating in the Winkler Bakery, I can't imagine doing that unless it was really chilly...the place is pretty warm. Go in, buy some Moravian sugar cake, some of the fresh bread and definitely try the Moravian sugar cookies, excellent treat but do take it outside to enjoy.
If you are interested in the arts, the district around Sixth and Trade streets is very nice. for a great meal try Sweet Potatoes on Trade.
If shopping is your thing, head to Reynolda Village. Have lunch at Simply Yummy or The Village Tavern.
If you are interested in stopping at Winston Salem, please post any additional questions. There are several regulars on the forum from that area.
Welcome to North Carolina!

PS if you want great ice cream in Winston Salem try Blue Ridge Ice Cream on Stratford Road. If gelato is your thing, go to Cafe Gelato on Reynolda Road at Hanes Park.

Now you tell me!!

Now you know for next time!

Our kids have a condo (second "home") just off Stratford near all that great shopping--it is urban living at its best!! Have you been to Green Gate Olive Oils? OMG--it is absolutely wonderful.

Actually, Gretchen, you put me on to Green Gate and the blood orange oil. Now I am a regular. They will mail a tasting packet of any combination of oils and vinegars. It was a great hit! Thanks for the tip. Amazing what you can still learn about your own hometown.

Ah, didn't remember that. REally about the tasting pack? Missed that.
That gelato gal gave out free samples at a tennis tournament at Hanes. It was SO good. I mean she stayed there for most of the day, and I was finally going to buy some--she said, no charge!!
I need to get a list of your other faves for eating for the kids. They will be up there a good bit this summer probably.

Guess what. I just went by a tony little shopping strip around the corner from me and lo and behold, an olive oil shop is opening. I wonder how it would go with tonic!! I'll have so much to use!!