Distance from Charlotte: 88 miles
This quiet town halfway between High Point and Greensboro was settled as a Quaker village in the eighteenth century. Its Oakdale Road entrance includes an old cotton mill on one side and schoolhouse on the other, setting its historical tone. Downtown, you'll find giant oak trees shading the streets full of cozy restaurants and small shops.
To dive into a full historical tour of Jamestown, start out at Perky's Café. It sits in one of the town's oldest buildings, which housed the local doctor's office and pharmacy throughout much of the twentieth century. The café's sunny dining room overlooks the old railroad, and you can fuel up with a house-baked pound cake, a breakfast burrito, and a coffee before heading out for the day. Can't make it there that early? Stop by later in the day for a smoothie in flavors like mango, pomegranate, and green apple. 105 W. Main St., 336-887-3460
Just a few blocks away from Perky's is the mendenhall Plantation, the heart of Jamestown's heritage. Built in 1811 by Richard Mendenhall, one of the town's earliest leaders and a tanner by trade, the plantation was one of Jamestown's many hiding spots for slaves on the Underground Railroad. You can still explore the main house, the barn where Mendenhall did his tanning, and even see a flat-bottomed wagon — one of the last in the country — that slaves would stow away in on their way north. 603 W. Main St., 336-454-3819
Back on Main Street, the shopping can begin with River Twist Gift, Garden, and Design. This charming shop is housed in the town's old Esso gas station, built in the 1930s. It's packed from floor to ceiling with covetable trinkets — you can take home a funky clock, an ornament from the room of old-fashioned Christmas décor, a bottle of North Carolina wine, or a candle from the Tyler Candle Co. Also head around the corner to visit The Soap lady — owner Susan Stringer makes her own molds in fragrances ranging from men's scents to a very girlish strawberry. Plus, peruse her selection of other locally made products including jewelry and pottery. River Twist Gift, Garden, and Design, 116 E. Main St., 336-887-5966; The Soap Lady, 116 C E. Main St., 336-883-7627
Southern Roots is your best bet for dinner (it's not open for lunch on Saturdays). Try to get a spot on the patio, where a brick fireplace and lounge seating make comfort dishes like the fried green tomatoes, seafood gumbo, and fried Cajun catfish even more comfortable. It doesn't take reservations and this cozy restaurant is usually full (especially on the weekends), so arrive early and enjoy a beer from the local Red Oak brewery at the bar while you wait. 119 E. Main St., 336-882-5570