Street Savvy: Greenwood

A bustling wine bar and a classic ice cream stand keep Old Town feeling young.

[1] Celebrate

Indulge your Downton Abbey fantasies at Sassafras, a tea room located in a historic home originally built for the town doctor. In addition to lunch, the popular place for baby and bridal showers serves The Duchess Tea—three varieties served with a tower of scones, finger sandwiches, and dainty desserts—six days a week. 229 N. Madison Ave., 317-888-8449,


[2] Shop

Brown County feels closer with Take Root and Carriage House Primitives, sister shops that carry countrified seasonal decorations. Favorites we haven’t spotted elsewhere include candles from throwback brand 1803 (check out the Biscuits & Honey scent) and felt flower–embellished table runners. 202 N. Madison Ave., 317-882-0497.

[3] Accessorize

Two sisters have turned their knack for crafts into Naykin Boutique, filling the store with homemade headbands, tutus, and oodles of custom bows and offering monthly workshops for kids. 199 N. Madison Ave., 317-881-4959, 


[4] Unwind

The best seat at Vino Villa is on the large patio of its historic house, but the top-floor bar inside is just as good for enjoying a glass of wine with friends. The menu includes pizza, small plates of muffuletta sliders and smoked duck breast, and the chef’s family-recipe carrot cake. Grab a bottle of wine to take home—if you can make up your mind: The first-floor shop contains more than 500 different labels. 200 N. Madison Ave., 317-882-9463,


IN THE KNOW: Jack Meeks
Owner of Happy Jack’s Hotdogs

Your cart is in the Main Street parking lot. Who stops by?
I get a lot of foot traffic: families, retirees, and almost everyone who goes into the barbershop across the street.
How’s the weather?
Challenging. If it’s colder than 32 degrees or too windy, I don’t go out.
What’s Greenwood’s favorite dog?
The Hill City hotdog with onions, our Southern-style relish, and spicy chili sauce.


[5] Dig In

The pan pizza at sports bar Blind Pig (slang for a divey speakeasy during Prohibition) makes you rethink the Neapolitan craze. The housemade crust  has golden, burnt-cheese edges, and the kitchen doesn’t skimp on fresh-tasting
mozzarella. 147 S. Madison Ave., 317-882-7892.

[6] Collect

Train aficionados young and old bond over the railroad memorabilia at A-Trains, Old Town’s newest shop. Owner Les Jarrett stocks engines priced up to $400 and accessories for diehard collectors, plus enough engineer kits, activity books, and train-themed DVDs to fill a caboose. 180 W. Main St., 317-881-5530,

[7] Snack

It’s not summer until you’ve been to Mrs. Curl Ice Cream Shop and Outdoor Cafe. The cash-only mom ’n’ pop has been a landmark for 51 years, with an oldies soundtrack, patriotic-colored tables, and “Curl Girls” handing out Teddy Graham–topped soft-serve cones. This month, try the “500” milkshake, with vanilla and chocolate sprinkles. 259 S. Meridian St., 317-882-1031,


Photos by Tony Valainis; illustration by Darren Johnson.

This article appeared in the May 2013 issue.