Mostly at the wineries, plus two Keswick traditions. The Keswick Hunt Club Horse Show is October 3, and the Blessing of the Hounds is Thanksgiving morning, November 26, at Grace Episcopal Church, free and open to the public. In between, Southwest Mountains Vineyards, Merrie Mill and Keswick Vineyards host concerts, Halloween nights and a holiday market.
A line-dancing lesson and wine in the barn at Southwest Mountains Vineyards. $12; reserve ahead
Ring classes, vendors and tailgating on the Hunt Club grounds, with an evening Hunt Night class. Tickets online
Local artists and a book fair at Merrie Mill Farm & Vineyard, 11 to 5:30
A film with table service at Southwest Mountains Vineyards, the last in the series. Reservations required
An oyster truck, live music from noon to 4 and wine at Keswick Vineyards, 12 to 5
A family Halloween day at Southwest Mountains Vineyards, 11 to 5:30, then a Spooky Wine Walk at 7:15 ($32)
A homecoming concert at Southwest Mountains Vineyards, 6 to 9. $25 in advance, $30 at the door
A costumed evening dance at Merrie Mill Farm & Vineyard, hosted by the Tom Tom Foundation. Ticketed
Thanksgiving morning at 10 at Grace Episcopal Church, a tradition since 1929. Free; arrive early to park
Wavelength plays Merrie Mill Farm & Vineyard, 1 to 4
A holiday market at Merrie Mill Farm & Vineyard, 11:30 to 5
Every event is from its host's own website or ticket page, checked September 29, 2026. The Hunt Club's October 4 hunter pace is cancelled.
On the Rivanna and the trails around Charlottesville. Milton Landing, off Route 250 east, is a free canoe launch; Darden Towe Park adds trails, a boat launch and a fenced dog park; and the 4-mile Saunders-Monticello Trail climbs no steeper than 5%.
End of Randolph Mill Ln, off Route 250 east
A free Rivanna River canoe ramp with trails, open sunrise to sunset, and one of the county's river launches along with Brook Hill and Darden Towe. The state has recorded 97 bird species here.
Park details1445 Darden Towe Park Rd, Charlottesville
A free county park on the east bank of the Rivanna, with a boat launch, hiking and bike trails, and a fenced 1-acre off-leash dog park. The state has recorded 146 bird species here.
Park detailsRoute 53 and Route 20 trailheads
Four miles to Monticello at a grade of no more than 5%, open to wheelchairs and bikes from sunrise to sunset.
Dogs on a leash; no e-bikes.
Trail details1435 Carters Mountain Trail, Charlottesville
Pick-your-own peaches from June to September and apples from mid-August to mid-December. The 2026 season runs to October 31, daily 9 to 6.
Weekend tickets are required September 12 to November 15 for ages 12 and up.
Visit the websiteThe trade-off: Keswick itself is private land and country roads. Its parks, river launches and trails are county and Monticello land toward Charlottesville.
Weekly winery music and a handful of yearly events. Keswick Vineyards has music every Saturday from noon to 4 and an oyster roast on October 11, 2026; and Monticello holds its free July 4 naturalization ceremony every year. For the Keswick Horse Show and the Blessing of the Hounds, see Equestrian Life.
Saturdays and Wednesdays, all year
Live music Saturdays from noon to 4 and “Wine Down Wednesday” from 5:30 to 8:30. Fall 2026 includes an oyster roast on October 11.
Event calendarMay, and August to October
Merrie Mill Farm & Vineyard stays open until 9pm on Fridays in those months for a music series.
Visit the websiteMonticello · every July 4
The 64th annual Independence Day naturalization ceremony in 2026 welcomed 75 new citizens from 35 nations. Free, but reservations are required, and 2026 sold out.
Event pageEvery September
A volunteer river cleanup held each September since 2020: 1,162 volunteers and 519 tires removed so far, per the Rivanna Conservation Alliance.
The 2027 date isn't posted yet.
Cleanup details| Event | When | Details |
|---|---|---|
| Historic Garden Week tour | Sunday, April 18, 2027 | The Albemarle-Charlottesville tour, 10 to 5; $50 in advance. The 2027 houses are in western Albemarle, not Keswick |
A whole historic landscape, mostly from the road. Keswick sits in the 31,000-acre Southwest Mountains Rural Historic District, listed on the National Register in 1992, where most properties are private. Castle Hill, from 1764, and Shadwell, where Thomas Jefferson was born in 1743, are both private; Monticello is the one you can tour.
Routes 22 and 231
About 31,000 acres and nearly 1,000 contributing buildings and sites, listed on the National Register in 1992.
Most properties are private; the National Park Service says to view them from public roads.
About the districtOff Route 231, Cismont
Built in 1764 by Dr. Thomas Walker, with a brick addition from 1823–24 for William Cabell Rives; later the home of novelist Amélie Rives.
A private residence, not open to the public.
About Castle HillRoute 250 east
Thomas Jefferson's birthplace, in 1743. The house burned in February 1770; a 1991 dig found two cellar foundations.
Privately owned, with no visitor site.
About Shadwell1050 Monticello Loop, Charlottesville
Jefferson's home. Its local memberships are open to residents of Albemarle, Louisa, Fluvanna and other nearby counties; in 2026, a grounds-only adult ticket is $22.
Local membershipMore on Keswick's old houses: Historic Estates in Keswick.
Around Grace Church, Keswick Hall and the county's libraries. Grace Episcopal Church holds Sunday services at 11am, and Keswick Hall's spa is open daily 9 to 6. Keswick has no library branch of its own; the nearest are in Charlottesville, and Louisa-side residents are closer to the Louisa County Library in Mineral.
5607 Gordonsville Rd, Keswick
Sunday services at 11am every week, plus 9am on the first, third and fifth Sundays, also livestreamed. The parish also has All Saints Chapel on Stony Point Road.
Visit the website701 Club Dr, Keswick
Open daily 9 to 6, with eight treatment rooms, a hair and nail salon and Valmont treatments.
The resort doesn't say whether non-guests can book; ask when you call.
Visit the websiteNorthside, 705 Rio Rd W · Central, 201 E Market St
The regional library has no Keswick branch. Northside is open until 9pm Monday to Thursday.
On the Louisa side, the Louisa County Library in Mineral is closer.
Library locationsSources: Keswick Vineyards; Merrie Mill Farm & Vineyard; Virginia DWR, Milton Landing; Albemarle County, boating and river access; Virginia DWR, Darden Towe Park (Bird and Wildlife Trail); Monticello, local membership.
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