This picturesque town in the Isle of Wight offers a look at our country’s history — along with gorgeous views, great dining options and fun holiday markets
by Addie Ladner
Less than three hours from Raleigh, you’ll find the Isle of Wight County in Virginia. This picturesque region offers a direct link to our country’s history thanks to the town of Smithfield, a colonial-era port along the banks of the James River. Established in 1643, it’s the site of our country’s oldest county government still in operation.
Over a weekend stay in Smithfield, you can soak up stunning architecture, from stately Georgian buildings to ornate Victorian residences — plus enjoy diverse cuisine, plenty of culture and beautiful riverfront views. This time of year, the Isle of Wight comes alive with fall color and lively events, making it a perfect autumnal destination for North Carolinians.
Where to Stay
George Washington himself once stayed at the historic Smithfield Inn (112 Main Street), a quaint eight-bedroom hotel that dates back to 1752. There, you can enjoy the on-site William Rand Tavern, with a cocktail program inspired by the inn’s lush, bountiful gardens. Right in the marina, Smithfield Station (415 S Church Street) offers a more lively stay with stunning views of the river, numerous common spaces and an on-site bar and restaurant serving seafood-forward cuisine. For fans of Victorian decorative arts, consider the Mansion on Main Bed & Breakfast (36 Main Street), an estate full of antique furniture and artwork that offers a luxurious trip back in time.
What to See
About 15 minutes from Smithfield’s downtown, soak up Fort Boykin (7410 Fort Boykin Trail) a nearly 20-acre park with views of the James River that dates back to the 1620s. Also a short jaunt outside of the town’s center, dating to 1685, St. Luke’s Historic Church & Museum (14477 Benns Church Boulevard) offers more than 40 acres of colonial gardens, a historic cemetery and the oldest brick church in Virginia. Right in town, the Isle of Wight County Museum (103 Main Street), features curiosities like the world’s oldest still preserved ham and peanut! And one could spend a whole day at the Windsor Castle Park (705 Cedar Street), a sprawling 200-plus-acre estate anchored by a historic manor with a variety of trails and picnic areas.
Savor & Sip
Smithfield might be best known as the pork capital of the world — it’s the headquarters for Smithfield Foods, after all, and you can find classic Southern dishes at Taste of Smithfield Restaurant (217 Main Street) — but the town has delicious, diverse offerings for any palate. A day might start at the regionally-owned Cure Coffeehouse (113 N. Church Street) with an espresso or matcha beverage and fresh breakfast items like fruit and yogurt parfaits and avocado toast. The Fiddlin’ Pig (100 Main Street) offers an authentic British pub experience and a solid weekend brunch menu; try its Scotch Egg, Traditional Fish & Chips or Shepherds Pie. For a global but laid back dinner, be sure to experience Chili Hill (302 Main Street), a locally run Thai inspired market and restaurant whose menu is informed by the owners’ nearby farm paired with authentic Asian delicacies.
Where to Shop
From art galleries to clothing boutiques to country stores, you’ll find a treasure trove of walkable locally-owned and -operated retailers on Main Street and its side streets. Among them: The Main Gourmet (223 Main Street), located inside the Hamtown Mercantile features a selection of artisan vinegars, cheese and picnic accoutrements; Vintage Potential (215 Main Street), where you can find a curated secondhand finds from typewriters to tea cups; The Christmas Store of Smithfield (108 Main Street), where you’ll find holiday magic, any time of year; and Color Scapes Fine Arts Gallery (343 Main Street), opened by the late artist Ann Hubbard and now run by her husband, is filled with Hubbard’s vibrant colorful delightful paintings among other pieces. For antiques, don’t miss Mansion House Art and Antique (102 N. Church Street), which is run by the folks at the Mansion on Main B&B.
When to visit
While the Isle of Wight is worth a trip any time of year, the fall and holiday seasons bring holiday markets that make it especially lively. The Autumn Vintage Market on September 27 is a street festival-style market that transforms Main Street into a haven for lovers of vintage, farmhouse and second-hand finds. In addition to nearly 100 vendors, visitors will also find local food and live music. On November 22, find the Mistletoe Market, a European-style market, also with 100 vendors, that starts in the afternoon and continues into the evening. It also boasts food and entertainment, including performances by the Southside Ballet (3 p.m.) and the Smithfield High School Choraliers (5 p.m.). Also don’t forget to pay Santa Claus a visit! The Market at the Manor at Windsor Castle Park on December 6, where you’ll also find seasonal items, warm beverages and food, crafts overlooking Cypress Creek.
This post was paid for by the Isle of Wight, Virginia.
This post was originally published on September 18, 2025 on waltermagazine.com
