Grape Stomp Maryland 2026: Crow Vineyard Event Guide

The 2026 Grape Stomp at Crow Vineyard & Winery takes place Sunday, September 20, from 12 to 5 PM in Kennedyville, Maryland — one of the most hands-on wine events in the state during harvest season. Visitors step into a barrel and stomp grapes, sample estate-grown wine, learn about the grape varieties on the property, and purchase additional food and wine throughout the afternoon. The event is part of Crow Vineyard's annual harvest celebration on their 365-acre working farm on Maryland's Eastern Shore. This guide covers what to expect, how to get there from Baltimore, and how to plan the trip for a couple, a friend group, or a larger outing.

Grape Stomp Maryland 2026: Date, Time & Location

Tickets are non-refundable. Check the winery's event page for current pricing and availability — harvest events here sell out as September approaches.

What Happens at the Crow Vineyard Grape Stomp?

This is not a typical winery visit. Instead of sitting in a tasting room, you're outside on a working farm during harvest season, participating in an activity that connects directly to how wine gets made.

Grape Stomping

The main event. You slip off your shoes, step into a barrel of grapes, and stomp. It's messy, physical, and genuinely fun — crushing grapes with bare feet is the oldest winemaking technique in the world, and it's the kind of hands-on experience unavailable at a standard tasting room visit. The grape juice and skins stain everything they touch, which is part of the appeal and why you dress accordingly.

Wine Tasting

Your ticket includes a tasting of three Crow Vineyard wines. The winery produces "New World" style wines from estate-grown grapes — varieties selected specifically for the Eastern Shore's Atlantic Coastal Plain terroir. Crow's Barbera Reserve has been recognized as one of the standout Maryland wines. Tastings happen alongside the stomping, so you can sip between stomps and get a real sense of what the vineyard produces.

Learning About Maryland Grape Varieties

Part of the Grape Stomp experience is learning which varietals Crow grows and how those varieties connect to the broader Chesapeake Wine Trail and Maryland wine landscape. The winery's staff and winemaker are typically on hand to answer questions about the growing process, harvest timing, and what makes Eastern Shore wine distinct from other Maryland wine regions.

Food and Additional Wine

Additional food and wine are available for purchase throughout the event. Crow Farm is known for grass-fed Angus beef and locally sourced charcuterie plates — the farm-to-table connection is real here, not a marketing line. The tasting room is open during the event for glass and bottle purchases.

Where Is Crow Vineyard & Winery?

Crow Vineyard & Winery sits on a 365-acre third-generation family farm in Kennedyville, Maryland — Kent County, on the upper Eastern Shore. The farm is 10 minutes north of historic Chestertown and 30 minutes south of Chesapeake City. It's part of the Maryland Wineries Association and the Chesapeake Wine Trail, the designated wine trail covering Maryland's Eastern Shore wine region.

The property includes the vineyard, a tasting room, farm trails, and a farmstay B&B in a renovated 1847 farmhouse — making it one of the few Maryland wineries where you can both visit for the day and stay overnight.

Is the Grape Stomp Worth the Trip From Baltimore?

Yes — but the trip works best when you plan it as a full day rather than a quick winery stop. The Grape Stomp runs from noon to 5 PM, and the Eastern Shore setting adds a dimension that makes the drive feel less like a commute and more like a genuine day trip. You're leaving the city for a working farm surrounded by open fields and vineyard rows in one of the quietest, most agricultural parts of Maryland.

The September timing helps too. Late September on the Eastern Shore is one of the best weather windows in Maryland — warm days, cooling evenings, harvest colors beginning, and none of the summer humidity that makes outdoor events uncomfortable.

How to Plan a Maryland Grape Stomp Trip

Going as a Couple

Drive yourselves or combine the trip with a night at Crow Farm's B&B — the farmstay puts you on the property, which means no driving after the event and a full Eastern Shore morning the next day before heading home. The B&B occupies the renovated 1847 farmhouse, with meals served family-style using farm-grown ingredients. Chestertown is 10 minutes south and offers waterfront restaurants and walks along the Chester River.

Going With Friends (4–10 People)

This is where group transportation starts making practical sense. A group of six to ten friends in an executive Sprinter van gets picked up at one meeting point, rides together to Kennedyville, spends the afternoon stomping and tasting, and rides home with wine purchases stored in the vehicle. Nobody drives, nobody navigates, and the ride itself becomes part of the day. The designated-driver problem disappears entirely — everyone participates in the tastings fully.

Going as a Larger Group (10–20 People)

Birthday groups, corporate outings, and larger friend gatherings use a limo bus or party bus. The vehicle accommodates the full group, handles the Eastern Shore route, and gives the group a social space between the event and the ride home. Bayside provides group wine tour transportation across the full Baltimore, Annapolis, DC, and Virginia service area. For parties of five or more, Crow Vineyard requests that you call their tasting room at 302-304-0551 to arrange your visit — a step worth handling before your transportation is booked.

Grape Stomp vs. a Regular Maryland Wine Tour

What Should You Bring to a Grape Stomp?

1. Clothes you don't mind staining. Grape juice gets on everything below the knee. Dark-colored, casual clothing is the move — leave the white sneakers at home.
2. Shoes that can get messy or sandals. You'll stomp barefoot in the barrel, but you'll want something for walking the farm property before and after. The grounds are outdoor and unpaved in places.
3. Layers for September weather. Late September in Maryland can range from warm afternoons to cool evenings. The event runs until 5 PM and temperatures drop as the afternoon fades.
4. Your ticket confirmation. Tickets are required and checked at arrival. Have your confirmation accessible on your phone or printed.
5. A plan for getting home. If you're tasting wine at the event, you need a sober driver or a vehicle with one. This is the single most practical reason groups book transportation to winery events.

Grape Stomp Maryland FAQ