Using the walking tour brochure and map you picked up at the visitor center, head out on the brick sidewalks to explore the historic part of Main Street, which runs for about 3/4 mile. It goes up and down two hills, so wear comfortable walking shoes.
Begin your tour at the Fields-Penn 1860 House Museum, at the corner of Main and Cummings streets (tel. 276/676-0216), which depicts how Abingdon's upper class lived in the mid-19th century (James Fields, who built it, was a bricklayer and building contractor; George Penn, who bought it in the 1890s, was a lawyer). The museum is open daily from 10am to 4pm and admission is free.
From there, you'll head west on Main Street through Abingdon's 3-block-long business district. Several antiques and collectibles emporia will vie for your attention, but keep going to Depot Square. Turn left there to the restored Abingdon Passenger Train Station, now home to the Historical Society of Washington County (tel. 276/628-8761; www.hswcv.org). Don't miss the small collection of dramatic railway photographs by O. Winston Link, whose work is also showcased in his museum in Roanoke. The station is open April to October Monday through Friday 10am to 4pm, Saturday 10am to 2pm (weekdays only Nov-Mar).
The old freight depot next door is now the Abingdon Arts Depot ★ (tel. 276/628-9091; www.abingdonartsdepot.org), where you can watch artists at work in their studios Thursday through Saturday January to March from 11am to 3pm and April to December from 10am to 4pm.
Now backtrack east along Main Street, where the Martha Washington Hotel & Spa, the Barter Theatre, and 30 other buildings and homes -- with birthdates ranging from 1779 to 1925 -- wait to be observed. At the bottom of the hill, a right turn on Pecan Street will take you to the western head of the Virginia Creeper Trail. Parked under a shed there is "Abingdon's Mollie," or officially Norfolk & Western Engine No. 433, similar to the steam locomotives that had such a tough time with the grade that they became facetiously known as the "Virginia Creeper."
Back on Main Street, turn right and walk up the next hill to the Star Museum, 170 E. Main St. (tel. 276/608-7452), containing a huge collection of celebrity memorabilia gathered by Abingdon native Robert Weisfeld, who lived in New York City for 16 years. Marilyn Monroe's red cocktail dress, Errol Flynn's swim trunks, and a copy of Michael Jackson's first Motown single ("I Want You Back") are well hidden among the items. None of them are labeled, so call in advance to arrange a guided tour by Robert. Admission is $10 adults, $5 children 12 and under.
Stop at the top of the hill and look up at the Tiffany stained-glass windows in the Washington County Courthouse, built in 1869 to replace an earlier version burned during the Civil War. The Tiffany windows were added as a memorial to World War I veterans. From here you'll head downhill again past The Tavern, considered the oldest building in town. Built around 1779 and used as a stagecoach inn and tavern, it's now home to one of the town's better restaurants. You can still see the mail slot in the original post office in an addition on the east side of the building.
On the west side of town, art lovers can visit the William King Museum, 415 Academy Dr. (tel. 276/628-5005; www.williamkingmuseum.org), which is very good at showcasing the region's cultural heritage. It also hosts visiting exhibits. There's also a good museum shop. Admission is $5 adults, $3 for seniors and students. The center is open Tuesday 10am to 9pm; Wednesday to Saturday 10am to 5pm; Sunday 1 to 5pm. The center is in a refurbished school building (turn uphill off West Main St. on Academy Dr. and follow the signs for arts-center parking).
The Wolves & Daniel Boone's Dogs -- After walking over Abingdon's second hill -- where the 1869 Washington County Courthouse stands -- you'll come to the Cave House, now home to the Holston Mountain Artisans. Behind the house is the cave from whence emerged the wolves that attacked Daniel Boone's dogs. It's not marked, but to find it, take the alley to the left of the house to a stop sign, and turn right. You can peer through lattice into the mouth of the cave, which is below a rickety old barn.
A Nearby Gristmill & A Winery
A scenic 4 1/4-mile drive leads from Valley Street in Abingdon through a picturesque valley to White's Mill (tel. 276/628-2960; www.whitesmill.org), built in 1790 and now on the National Register of Historic Places. It's owned by a nonprofit foundation, which is slowly restoring its 22-foot diameter steel wheel and original grinding stone. Admission is by donation, and it's open Wednesday through Sunday 10am to 6pm. Closed January and February. You can buy meal from the mill's electric grinders. A shop across the road sells local handcrafts.
In rolling hills about 7 1/2 miles east of town, Abingdon Vineyard & Winery (tel. 276/623-1255; www.abingdonwinery.com) is open for tasting its reds and whites from March 15 to December 15, Tuesday to Saturday 10am to 6pm, Sunday noon to 6pm. Follow U.S. 58 east 5 miles past I-81, turn right on Oseola Road (S.R. 722), and follow the grape cluster signs 2 1/2 miles to the winery.
Note: This information was accurate when it was published, but can change without notice. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.