For Farmington, the resort across Ivy Road has a November calendar with an unusual shape. Its three biggest events come in sequence. Each one is held a little farther from the building than the one before, and each one raises money for a different cause. Professional tennis opens the month on the indoor courts at Boar's Head Sports Club. In the middle of the month the action moves outdoors, onto a half-mile lighted trail across the resort grounds. On Thanksgiving morning it leaves the property entirely and runs through the surrounding neighborhoods on foot.
Read in order, the month shows the resort stepping a little farther out each week, with a different beneficiary attached to each step. The dates below are for 2026, counted from early October, with a little more than three weeks before the first serve.
Week One Is Played Indoors
The Jonathan Fried Men's Pro Challenger runs November 2 through 8, 2026, Monday through Sunday, according to the ATP Tour's tournament listing. Boar's Head calls it an indoor men's tournament that draws top-100 talent from around the world, played on the indoor courts at Boar's Head Sports Club, and it benefits Special Olympics Virginia.
The event's real character shows in its champions list. The ATP archive lists winners back to 2009, and a good number of the names went on to bigger stages:
- 2025: Rafael Jódar
- 2024: James Trotter
- 2023: Beibit Zhukayev
- 2022: Ben Shelton
- 2018: Tommy Paul
- 2016: Reilly Opelka
- 2012: Denis Kudla
Ben Shelton and Tommy Paul both won this title on these indoor courts. For a neighbor, that is the case for going in person. A Challenger is where players show up on the way to somewhere else, and the courts are a short drive from home.
The 2026 spectator details are still unpublished. The ATP listing gives no ticket prices or session times for this year. CBS19's coverage of a prior edition reported free admission through Thursday that year. That is useful history, but the 2026 terms have not been confirmed.
The Quieter Days After the Final
Once the tennis wraps on Sunday, November 8, the resort's November calendar fills the gap with smaller, indoor events. A Holiday Watercolor Workshop runs that same Sunday from 11 a.m. to 2 p.m., and a second one is set for November 29. Music in The Mill Room plays Wednesdays and Fridays from 5:30 to 8:30 p.m., which gives the weekday evenings between the big events a regular fixture.
The series starts before November for anyone who wants an earlier start. The resort's calendar lists Watercolor Workshops on October 11 and October 25, also from 11 a.m. to 2 p.m.
These four days are the last stretch of the month that happens entirely indoors. On Friday the events move outside.
Week Two Moves Onto the Grounds
Winter Wander opens Friday, November 13, 2026, for its sixth year. It runs on select nights through the holidays and closes January 2, 2027. The 2026 ticket page lists what is new this year. Lattice Lane gets a new light-wrapped tree and an entirely new program. Glistening Grove, a field of more than 700 light poles each choreographed to music, returns with two new songs. Two new live dance shows, The Greatest Glow and Jingle Jam, play in the Enchantment District on select nights.
Opening weekend has its own focus. The resort calendar lists Winter Wander Dog Nights for November 13 through 15, from 5 to 8:30 p.m.
The trail is the biggest stretch of the grounds that any event covers all year. The Winter Wander FAQ puts it at just over half a mile, about a quarter-mile walk from parking, and says a typical visit takes 30 to 45 minutes. The details that matter most before a first visit:
- Entry windows are strict. Unless it is a Winter Wander+ ticket, each nightly ticket is good for a 30-minute arrival window. Guests can stay until closing once inside.
- Prices rise on the day of the event. The ticket page sorts nights into Value, Regular and Prime tiers and says prices increase on event day.
- It is cashless. The 2026 ticket page says credit card payments only.
- Parking is free. According to the know-before-you-go page, staff direct drivers to nearby lots, and there is a drop-off for guests who can't walk from parking.
- Transfers close the night before. Tickets must be transferred online by 11:59 p.m. the evening before. Same-day transfers aren't allowed.
- The surface is accessible. The trail is outdoors on a hard surface that works with most strollers and wheelchairs.
The giving changes with this event, too. The tennis week supports one organization. At Winter Wander checkout, guests can add a donation for six: Big Brothers Big Sisters of the Central Blue Ridge, the Blue Ridge Area Food Bank, the Charlottesville Free Clinic, Habitat for Humanity, the Boys and Girls Clubs of Central Virginia and the Charlottesville-Albemarle SPCA.
Thanksgiving Morning Reaches the Streets
The month's last big event goes past the edge of the property. The 45th annual Boar's Head Turkey Trot 5K starts at 9 a.m. on Thursday, November 26, and benefits UVA Health Children's. Its race listing says the course starts and ends at the resort, "winds through the surrounding neighborhoods and is very hilly." After a month of tennis indoors and lights on the grounds, the final event takes place on the roads outside the resort.
The race has been growing. NBC29 reported that the 2022 race drew about 1,200 participants and raised more than $20,000 for UVA Children's. The station reported more than 1,700 participants a year later, at the 2023 race.
Registration for 2026 is open. The 5K costs $45, and the price goes up after 11:59 p.m. on Wednesday, November 18. Tiny Turkeys, a free quarter-mile dash for children eight and under, takes registrations until 9 p.m. on November 25. Every 5K registrant gets a long-sleeve shirt.
The rest of the holiday is planned around the race. The resort lists a Thanksgiving Feast from 10 a.m. to 2 p.m. and Thanksgiving in The Mill Room from 3 to 9 p.m., so the day can run from the finish line straight to the table without leaving the property.
The Month in Order, and One Stop on Ivy Road
The calendar, start to finish:
- November 2 to 8: Jonathan Fried Men's Pro Challenger, indoor courts, for Special Olympics Virginia.
- November 8: Holiday Watercolor Workshop, 11 a.m. to 2 p.m.
- November 13: Winter Wander opens, with Dog Nights through November 15.
- November 18: Last day before the Turkey Trot 5K price increase.
- November 26: Turkey Trot at 9 a.m., then Thanksgiving service at the resort.
- November 29: Second Holiday Watercolor Workshop.
Winter Wander goes on after November ends. The December calendar lists a Drone Night on Monday, December 21, from 5 to 8 p.m. The ticket page describes it as a 200-drone show called Elevation Illumination, presented by CHO Airport. A Fireworks Finale follows on December 31 at 8 p.m.
For an evening before or after any of these, SugarBear Ice Cream's second shop is at 2405 Ivy Road, next to Bellair Market and Selvedge Brewing. CBS19 reported that the new shop has indoor seating. Its posted hours are noon to 9 p.m. on Sunday and Tuesday through Thursday, and noon to 10 p.m. on Friday and Saturday.
At Loring Woodriff Real Estate, we keep track of what happens around the neighborhoods we serve, including the calendar across Ivy Road from Farmington. If you'd like to talk about this corridor or the homes near it, let's work together.
