Western Loudoun

Seasonal guide

What the season brings.

The traditions that fall in this season, the farmers markets, and everything dated from now to the season’s end. The page changes with the season on its own.

Fall 2026, through November 30

This season out west

Rebuilt every morning from the same calendars as the weekend board.

Farmers markets

  • Leesburg Farmers Market, 30 Catoctin Circle SE (Virginia Village Shopping Center), Leesburg. Saturdays, 8 a.m. to noon (summer hours, May to October). Open year-round. Winter hours: see the market’s site. The market’s site
  • Purcellville Farmers Market, Town lot at Hatcher Ave. and Main St., Purcellville. Saturdays, rain or shine, 9 a.m. to noon. 2026 season opened May 9. The market’s site lists 25 Saturdays but no closing date. The market’s site

Dated listings this season

  1. Saturday, Oct. 17 to Oct. 31 · Wine

    Daydream Days

    Bluemont Vineyard · Bluemont

  2. Saturday, Oct. 17 to Oct. 31 · Farm

    Pumpkin picking

    Great Country Farms · Bluemont

  3. Saturday, Oct. 17 · Fair

    Fall Festival by Joshua's Hands

    Town of Purcellville · 10 a.m. to 5 p.m. · Purcellville

  4. Saturday, Oct. 17 · Wine

    B.Y.O.W. Party

    8 Chains North Winery · 1 to 3 p.m. · Waterford

  5. Saturday, Oct. 17 · Music

    Live Music with Karen Jonas

    8 Chains North Winery · 1:30 to 4:30 p.m. · Waterford

  6. Saturday, Oct. 17 · Music

    LIVE MUSIC: Shane Gamble

    Doukénie Winery · 2 to 5 p.m. · Hillsboro

  7. Saturday, Oct. 17 · Arts

    Tyler Reed: Magic That Connects

    Franklin Park Arts Center · 4 to 5:30 p.m. · Purcellville

  8. Saturday, Oct. 17 to Oct. 24 · 21 and up

    Adult corn maze night

    Great Country Farms · 6 to 9 p.m. · Bluemont

  9. Sunday, Oct. 18 · Wine

    Paws & Paint: Paint Your Pet

    868 Estate Vineyards · 1 to 3:30 p.m. · Hillsboro

  10. Sunday, Oct. 18 · Music

    Sunday Live Music feat. David Thong

    Dirt Farm Brewing · 1 to 4 p.m. · Bluemont

  11. Sunday, Oct. 18 · Music

    Live Music with Ryan Sill

    8 Chains North Winery · 1:30 to 4:30 p.m. · Waterford

  12. Sunday, Oct. 18 · Music

    Live Music: Ty Burkhardt

    Doukénie Winery · 2 to 5 p.m. · Hillsboro

  13. Monday, Oct. 19 · Arts

    Life Model Sketching Class

    Franklin Park Arts Center · 11 a.m. to 2 p.m. · Purcellville

  14. Wednesday, Oct. 21 · Arts

    Free to Create Art Day

    Franklin Park Arts Center · 11 a.m. to 3 p.m. · Purcellville

  15. Wednesday, Oct. 21 · Arts

    Start Lunch with the Arts: Still Life

    Franklin Park Arts Center · noon to 1:15 p.m. · Purcellville

  16. Wednesday, Oct. 21 · Games

    Trivia Night

    8 Chains North Winery · 6:30 to 8:30 p.m. · Waterford

  17. Wednesday, Oct. 21 · Music

    Music For Dessert: Kristin Rebecca

    Franklin Park Arts Center · 7 to 7:45 p.m. · Purcellville

  18. Thursday, Oct. 22 · Games

    Trivia Night with A+ Trivia

    Dirt Farm Brewing · 7 to 9 p.m. · Bluemont

  19. Friday, Oct. 23 · Out west

    Halloween Zip Tour

    Salamander Middleburg · all day · Middleburg

  20. Friday, Oct. 23 · Out west

    Hocus Pocus 2 Movie Night

    Wheatland Spring · all day · Waterford

  21. Friday, Oct. 23 · Wine

    Bottle & Board

    8 Chains North Winery · noon to 9 p.m. · Waterford

  22. Saturday, Oct. 24 · Out west

    Halloween in Lovettsville Community Park

    Loudoun County Parks, Recreation and Community Services · all day · Lovettsville

  23. Saturday, Oct. 24 · In town

    Zumba Party in Pink

    Town of Purcellville · 10 a.m. to noon · Purcellville

  24. Saturday, Oct. 24 · Fair

    Post Harvest Festival!

    Doukénie Winery · 11 a.m. to 6 p.m. · Hillsboro

  25. Saturday, Oct. 24 · Music

    Live Music with Lindsay Austin

    8 Chains North Winery · 1:30 to 4:30 p.m. · Waterford

  26. Saturday, Oct. 24 · Music

    Live Music: Bearded Harmony

    Doukénie Winery · 2 to 5 p.m. · Hillsboro

  27. Saturday, Oct. 24 · Arts

    Last Ham Standing presents “Comedy Royale”

    Franklin Park Arts Center · 8 to 10 p.m. · Purcellville

  28. Sunday, Oct. 25 · Outdoors

    Waterford Bicycle Classic

    Waterford Foundation · all day · Waterford

  29. Sunday, Oct. 25 · In town

    American Red Cross CPR Training

    Town of Purcellville · 11 a.m. to 1 p.m. · Purcellville

  30. Sunday, Oct. 25 · Market

    Howl-O-Ween: Dog Costume Contest + Market on the Mountain

    Dirt Farm Brewing · 11 a.m. to 4 p.m. · Bluemont

  31. Sunday, Oct. 25 · Wine

    Fall-Themed Wine Glass Paint & Sip

    8 Chains North Winery · noon to 2 p.m. · Waterford

  32. Sunday, Oct. 25 · In town

    Discover Nature's Secrets Monthly Nature Walk

    Town of Purcellville · 1 to 11:59 p.m. · Purcellville

  33. Sunday, Oct. 25 · Music

    Sunday Live Music feat. Logan Moore

    Dirt Farm Brewing · 1 to 4 p.m. · Bluemont

  34. Sunday, Oct. 25 · Music

    Live Music with Grayson Moon

    8 Chains North Winery · 1:30 to 4:30 p.m. · Waterford

  35. Sunday, Oct. 25 · Music

    Live Music: Sarah Cooper

    Doukénie Winery · 2 to 5 p.m. · Hillsboro

  36. Wednesday, Oct. 28 · Arts

    Tanglewood Marionettes: The Dragon King

    Franklin Park Arts Center · 10 to 11 a.m. · Purcellville

  37. Wednesday, Oct. 28 · Games

    Trivia Night

    8 Chains North Winery · 6:30 to 8:30 p.m. · Waterford

  38. Friday, Oct. 30 · Wine

    Bottle & Board

    8 Chains North Winery · noon to 9 p.m. · Waterford

  39. Saturday, Oct. 31 · Out west

    Hot Dog: It’s Halloween!

    Middleburg Community Center · all day · Middleburg

  40. Saturday, Oct. 31 · Out west

    Pumpkin Village

    Leesburg Animal Park · all day · Leesburg

  41. Saturday, Oct. 31 · Outdoors

    Hiking Meet-Up on The Trails at Dirt Farm

    Dirt Farm Brewing · 10:30 a.m. to 12:30 p.m. · Bluemont

  42. Saturday, Oct. 31 · Wine

    Last Heritage Club Day of 2026!

    Doukénie Winery · noon to 8 p.m. · Hillsboro

  43. Saturday, Oct. 31 · Music

    Live Music with David Andrew Smith

    8 Chains North Winery · 1:30 to 4:30 p.m. · Waterford

  44. Saturday, Oct. 31 · Music

    Live Music: Deane & Eric

    Doukénie Winery · 2 to 5 p.m. · Hillsboro

  45. Saturday, Oct. 31 · Food

    Halloween Beer Dinner at Dirt Farm

    Dirt Farm Brewing · 6 to 8 p.m. · Bluemont

  46. Sunday, Nov. 1 · Music

    Live Music with Gary Smallwood

    8 Chains North Winery · 1:30 to 4:30 p.m. · Waterford

  47. Sunday, Nov. 1 · Music

    Live Music: Jason Masi

    Doukénie Winery · 2 to 5 p.m. · Hillsboro

Checked Oct. 15 From the hosts’ own calendars, the towns’ and Visit Loudoun’s. Check with them before you go.

More to plan with

The events page lists the next 60 days with a town filter. The traditions page has the whole year. The itineraries are day plans built from the directory.