ROUND HILL
Williams Gap Vineyard
We enjoy the wine and setting on an ordinary afternoon, and the events are another reason to return. Check the winery’s current listings when choosing a date.
See current eventsLOCAL EVENTS
Events in wine country
A tasting, live music or a downtown festival can be a good starting point for your visit. These are the winery calendars, Purcellville events and seasonal picks we suggest checking first.
At Williams Gap and Walsh
PURCELLVILLE
Walsh Family Wine
Wine classes, dinners and other gatherings add to what we enjoy about Walsh. Look at the calendar for an event that suits your interests.
See current eventsDOWNTOWN & AROUND TOWN
Purcellville events
Main Street’s festivals, markets and block parties sit alongside the town’s arts, outdoor and holiday events throughout the year. Leave room for one between tastings, or build a visit around it.
Town of Purcellville
Hail to the Trail
1–4 p.m.
A free afternoon at Chapman DeMary Trail with nature activities, local environmental organizations and live music.
Town event detailsTown of Purcellville
Celebrate Purcellville
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See the program for times
A town-wide celebration highlighting local businesses, artists, performers and community organizations. Check the program when planning your visit.
Town event detailsTown of Purcellville
Purcellville Artisan Tour
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See the tour guide for times
Make the artisan tour part of a November weekend in Purcellville. Check the official tour guide for participating locations and opening times.
Town event detailsTown of Purcellville
Town Tree Lighting
6:30 p.m.
The town’s holiday celebrations begin with the tree lighting at Town Hall. Pair it with dinner in Purcellville.
Town holiday programPurcellville Main Street
A Miracle on 21st Street
1–6 p.m.
Main Street’s holiday festival and market on North 21st Street. Follow the organizer’s announcement for vendor and program details.
Main Street announcementTown of Purcellville
Holidays in Purcellville
Parade at noon · Market noon–6 p.m.
The town’s holiday parade and a market at Bush Tabernacle, with local artists, crafters and a LEGO display. A separate celebration from Main Street’s December 5 event.
Town holiday programMAIN STREET EVENTS
Purcellville Main Street
Downtown gatherings from the independent Main Street organization. Follow its announcements for the next festival or market.
BROADER TOWN EVENTS
Town of Purcellville
Arts, festivals, outdoor activities and holiday celebrations across town. The official calendar includes additional community events.
Town events & activitiesCurated selections · Checked August 30, 2026 against organizer announcements and calendars. Listings do not automatically sync; past events disappear after their final date. Confirm details with the organizer before visiting.
September–October 2026
Late summer and the start of fall
There is still time for an outdoor concert, while October brings the Waterford Fair. Choose the event first if it is central to your weekend, then arrange tastings and meals around it.
Music · Leesburg
Tarara’s remaining summer concerts
Aug 30 – Sep 26, 2026
The 2026 Saturday concert series continues through September 26. Check the lineup, ticket terms, and weather policy, and arrange transport before adding a concert to a tasting day.
Details & tickets ↗Brewery music · Lucketts
September music at Vanish
Sep 1 – Sep 30, 2026
Vanish’s September calendar lists daytime and evening performances. Choose a specific date from the organizer’s schedule and check food service before building the visit around a meal.
Details & tickets ↗Festival · Waterford
Waterford Fair
Oct 2 – Oct 4, 2026
The October 2–4 fair brings craft demonstrations, historic properties, art, and music to Waterford. Give the fair its own block of time; a winery visit should fit around it rather than make the day rushed.
Details & tickets ↗More calendars around the region
Seasonal picks are selected by VWE; calendar links open the organizers’ websites. Stone Tower’s feed updates when opened. Confirm dates, tickets and any age or membership restrictions directly.