Crossroads Inn
 
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 Experiences

Our historic Inn will provide you and your guests with a unique opportunity to experience the best of Charlottesville and the surrounding area. Let us curate your custom itinerary for an unforgettable stay. Whether you’re looking for best-in-class food, fun, or culture, Charlottesville has an experience for everyone in our 72-Hour Guide.

 
 
The Estate Tour and Tasting at Pippin Hill.

Estate Tour & Tasting

Head up the hill for a unique, in-depth exploration of Pippin Hill’s wines, vines, and garden-to-table cuisine. Experience an exclusive estate tour, an intimate tasting of 6 reserve wines paired with small bites, and a seated portion with a few signature dishes.


Enjoy a cooking class at Pippin Hill as you stay at the Crossroads Inn.

Cooking Classes

Sharpen your culinary skills through hands-on classes with helpful pointers and tricks of the trade. From making homemade pasta to seasonal soups, chef will butter up your culinary IQ! A deliciously fun way to spend an evening; great for groups or date nights.


The Crossroads Inn offers for you and your friends or loved ones to enjoy a private dining experience.

Vintner’s Table

We welcome your party of 10 or more to indulge in a custom 4 or 5-course pairing of Pippin Hill wines with chef’s inspired menu offerings. This intimate private event features dishes showcasing just-harvested ingredients sourced sustainably and locally.