Sip & Shop Holiday Weekend

Halifax County, VA

Charles Bass House

Rest & Relax at the Charles Bass House

Located in the heart of South Boston’s Historic District, this 1909 Queen Anne home is within walking distance of the shops, restaurants, and attractions of Downtown South Boston. Enjoy a quiet evening relaxing on the deck or in the hot tub. Then retire to the guest suite with a sitting room and private bath. Breakfast will be waiting for you in the morning to get your day going.

South Boston, VA |

Downtown South Boston

Festive Shopping in Downtown South Boston

Shop small for all the special people on your holiday gift list. Stroll up and down Main Street as you visit local shops and boutiques.

South Boston, VA |

The Prizery

Sights & Sounds at The Prizery

Enjoy the annual Festival of Trees fundraiser at the Prizery. Stop by before the show to view the competition of decorated trees, wreaths, centerpieces and gingerbread houses — guaranteed to put you in the holiday spirit! Then delight at the sounds of the holidays with the Danville Symphony Orchestra.

South Boston, VA |

Hunting Creek Vineyards

Wine Pours at Hunting Creek Vineyards

Taking the wine from “ground to the glass,” Hunting Creek Vineyards is the perfect place to stop and enjoy the moment. Located in the country on five acres of rolling hills, Hunting Creek Vineyards offers a variety of wines — there’s a sip for everyone!

Clover, VA |

Factory Street Brewing

On Tap at Factory Street Brewing Co.

Located in a historic 1920s tobacco prizery, Factory Street Brewing Co. has been renovated and decorated to highlight the unique history of this agricultural community. Celebrate the spirit of handcrafted beverages by sampling craft brews.

South Boston, VA |

Southern Plenty French Toast

Mimosa Breakfast at Southern Plenty

Kick off your day of festive shopping with a mimosa tasting and breakfast at the eclectic Southern Plenty Cafe. With home-baked pastries and a handcrafted menu (for both breakfast and lunch), there’s a palate-pleasing option for everyone.

South Boston, VA |

Dinner for two at Molasses Grill. Red wine and appetizers by candle light.

Craft Cocktails & Dinner at Molasses Grill

Sip on a handcrafted cocktail while you wait for your expertly prepared and locally sourced meal. This family-owned and -operated restaurant has been serving Southern-inspired cuisine for nearly 20 years. You can’t go wrong with the selection of extraordinary food, remarkable drinks, and awesome vibes.

Halifax, VA |

Main Street Bar & Grille Burger

Downtown Dinner at Main Street Bar & Grill

With classic American fare and everything from fresh, flame-grilled burgers and perfectly seared steaks to delectable desserts, there is surely something to please the palate at the Main Street Bar & Grill.

South Boston, VA |