The Perfect Couple’s Weekend in Culpeper, VA
December 8, 2025 Food & Drink Places to Stay Things to Do
Culpeper, VA is a dreamy choice for a two-day couples getaway equal parts cozy, tasty, and easy to explore. Picture charming accommodations you’ll actually want to linger in, excellent restaurants for date-night dinners, laid-back cafes for slow mornings, and a craft beverage scene that includes both local breweries and award-winning wineries. Add in a walkable downtown packed with character and a whole lot of history woven through the streets, and you’ve got the kind of weekend that feels like a reset without requiring a big trip.
Whether you’re celebrating something special or just craving quality time away from your usual routine, Culpeper delivers a little bit of everything: sip-and-stroll afternoons, scenic drives, and plenty of “let’s do one more stop” moments. Below is one two-day itinerary (of many!) to help you start planning—use it as a plug-and-play schedule or a flexible guide you can tailor to your pace, interests, and appetite.
Day 1
11:00 am – Stroll through the beautiful downtown of Culpeper. Enjoy shopping at the unique specialty shops.
12:30 pm – For lunch, head to Old House Vineyards, a fun and unique brewery, winery, and distillery with great food options from Green Ribbon, and excellent craft beverages!
2:30 pm – Relax and enjoy a couples massage at Collage Spa.
4:00 pm – Check into the cozy Botanical Oasis in Downtown Culpeper, and freshen up for dinner.
6:30 pm – Enjoy a short stroll across the street and have a delicious dinner at the Piedmont Steakhouse. The 1890’s historic brick building, features main and balcony level dining as well as a cozy bar and lounge area. The vibe is simply amazing.
8:00 pm – Head back in for the night and relax by the cozy wood-burning fireplace.
Day 2
9:00 am – Enjoy coffee and breakfast at Raven’s Nest Coffee House.
10:30 am – Embark on a morning hike on a trail at the Brandy Station Battlefield.
12:30 pm – Visit a real bean-to-bar chocolate workshop offering handmade chocolates at Cocoa Manna.
1:30 pm – Enjoy lunch at Sweet Roux Restaurant & Bar.
2:30 pm- Take a short stroll down Davis Street and explore the Culpeper Museum of History.
4:00 pm – Visit Vinosity for a wide variety of fine wines and growing selection of specialty food items.
5:00 pm – Cross the street and head to State Climb to challenge your partner to a rock climbing experience.
7:00 pm – Head next door for a casual dinner and some creative cocktails at Grill 309.
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