Posted by on September 30, 2017

40+ Things to Do in Middleburg, Virginia, in October

— There’s nothing quite like fall in Middleburg. The changing of the leaves adds dramatic colors to our scenic countryside, making it the perfect time to spend some time enjoying the region’s natural beauty, whether that means taking a trail ride, going for a hike, relaxing at a local winery or even just driving around. October is also home to some of Middleburg’s most popular annual events, including the Mosby Heritage Area Association’s Civil War conference, the Virginia Fall Races, Middleburg Film Festival and Halloween festivities at the Middleburg Community Center. Here’s our look at what’s going on in October:

National Sporting Library and Museum Middleburg VA1. “The Horse and the Camera: From the Judith & Jo Tartt, Jr. Photography Collection” at the National Sporting Library & Museum: Through Jan. 7, 2018

Capturing the horse at rest and in motion has been an obsession for many since the advent of the camera. From the first frames of a horse at full gallop from Edweard Muybridge’s Animal Locomotion and well into the 20th century, photographers were fascinated with the imagery of a horse standing still and the grace and power of equine movement. This exhibition shows a brief timeline of vintage and antique equine photographs from the pinnacle of black-and-white photography on loan from the private collection of Judith and Jo Tartt Jr. Guests to the NSLM will experience the changes in photographic imagery and horsemanship over the course of a century! The museum is open Wednesday-Sunday 10 a.m.-5 p.m.

2. “The Horse in Ancient Greek Art” at the National Sporting Library & Museum: Through Jan. 14, 2018

“The Horse in Ancient Greek Art” features Greek vases, sculpture, and coins from the 8th through the 4th centuries BCE drawn from private collections, the Virginia Museum of Fine Arts, the Tampa Museum of Art, and other museum collections. The exhibition and accompanying publication explore the significance of the horse in ancient Greek culture, and imagery of the horse in ancient myth, war, sport, and competition. From some of the earliest examples of the horse in Greek art, to stunning examples of black and red-figure vases, the objects on view illustrate ancient equestrian life. The museum is open Wednesday-Sunday 10 a.m.-5 p.m.

3. PaintNite! at Three Fox Vineyards: Oct. 1, 15 & 29 | 2 p.m.

Enjoy a fun afternoon of painting and drinking with your friends or meet new friends and experience something new! Please arrive 15 minutes early to check in and get settled. The session begins promptly at 2 p.m. All participants must be 21 or older. $45 per person (does not include drinks or food). Wine and bottle specials available to participants.

4. Live Music at Greenhill Winery & Vineyards: Oct. 1, 7-8 & 14-15 | 2-5 p.m.

Enjoy live music from 2-5 p.m. while sipping your favorite Greenhill wines! October’s lineup includes:

  • Oct. 1: Emily Rose
  • Oct. 7: Alan Gant
  • Oct. 8: Madeleine & Olivia Rudeen
  • Oct. 14 & 15: Terbush & Hannah

Salamander Resort Middleburg VA Yappy Hour5. Yappy Hour at Salamander Resort & Spa: Oct. 3 | 5-7 p.m.

Treat your dog and yourself to Salamander’s weekly Yappy Hour! Watch as your pooch tests their skills in the obstacle course, while you indulge in a special menu from Gold Cup Wine Bar featuring Sharing Chow including their Pimento Cheese “Hush Puppies” and a refreshing Pup-tail Menu with their Spicy Pup-arita with Blanco tequila. A portion of the proceeds are donated to the Middleburg Humane Foundation.

Dogs must remain on a leash at all times. Weather dependent.

6. Free Admission at the National Sporting Library & Museum: Wednesdays & Oct. 29

Enjoy free admission at the National Sporting Library & Museum every Wednesday and the last Sunday of every month.

7. Gallery Talk at the National Sporting Library & Museum: Oct. 4 | 2-2:30 p.m.

Each week, NSLM’s Clarice & Robert H. Smith educator or museum curators will give attendees a personalized sneak peek at traveling exhibitions, permanent collections, and the fascinating stories behind the works in the museum’s art collections. No two tours are alike, so come back for more! Reservations are not required and admission is free. Bring your friends! Gallery talks are every Wednesday at 2 p.m.

8. John Nilsen in Concert at Middleburg United Methodist Church: Oct. 4 | 6 p.m.

Composer and pianist John O’Conor will perform at Middleburg United Methodist Church as part of the MUMC music program.

Admission is free. Donations are welcome.

9. “The Environmental and Equestrian Tradition at Montpelier” at the National Sporting Library & Museum: Oct. 5 | 6-7:30 p.m.

Join us for a special evening event with Kat Imhoff, president of The Montpelier Foundation. Imhoff will discuss how James Madison’s environmental stewardship and Marion duPont Scott’s equestrian passion shape Montpelier’s landscape and mission today. For more information, click here.

$5 admission, free to NSLM members. RSVP to Anne Marie Barnes, the Clarice & Robert H. Smith educator, at or 540-687-6542 ext. 25.

Mosby Heritage Area Association10. Mosby Heritage Area Association Civil War Conference: Oct. 6-Oct. 8

Since 1998, the Mosby Heritage Area Association has offered an annual three-day conference examining the Civil War in Virginia, Maryland, and Pennsylvania through the lens of leadership as well as historic preservation. MHAA brings vetted experts with links to both the leaders of the Civil War and the battlefields and landscapes on which their actions played out.

Meeting at the classically handsome Middleburg Community Center, where President John F. Kennedy once attended church, conference attendees are provided with eight provocative talks on the annual topic beginning the Friday night of the conference and ending with a panel discussion of these historians on Saturday, followed by an evening banquet. Sunday, the final day of the conference, several of the historians will take us by luxury bus into the field to walk the ground and note the preservation efforts involved as we go.

Download the 2017 conference brochure here. For more information or reservations, call the Mosby Heritage Area Association at 540-687-6681.

11. Columbus Day Weekend at Three Fox Vineyards: Oct. 6-9

Celebrate with Three Fox! Play bocce on their vine-side courts. Get a great discount on wine and merchandise purchases for wearing the Italian colors or showing a Knights of Columbus, Sons of Italy, or similar card!

12. 10th Annual “Alpaca Day” at Three Fox Vineyards: Oct. 7

Three Fox will have the alpacas of Middleburg from the Flowing Fleece Farm visit for the day, so you can pet the alpacas and enjoy your lunch!

Empower Adventures Pumpkin Drop Middleburg VA13. Pumpkin Carving at Salamander Resort & Spa: Saturdays | 3 p.m.

Decorate with stickers, paint or carve a toothless grin on your own pumpkin to take home. $25 per pumpkin. For reservations, please call 540-326-4060.

14. Middleburg Farmers Market: Saturdays | 8 a.m.-noon

The Middleburg Farmers Market runs May 6-Oct. 28, every Saturday from 8 a.m.-noon in the gravel parking lot behind the Middleburg Community Center. Call 540-687-5152 for more info.

15. Slater Run Vineyards Open to the Public: Saturdays & Sundays | Noon-6 p.m.

Enjoy tastings, tours and beautiful views of hunt country at Slater Run Vineyards. They will be open from noon-6 p.m. on the first Saturday and Sunday of the month in September and every weekend in October.

16. Cooking Classes at Salamander Resort & Spa: Saturdays | 2-4 p.m.

Learn from the experts at Harrimans Cooking Studio. $79 per person. For reservations, please call 540-326-4070. October’s lineup includes:

  • Oct. 7 | Pasta Perfection Class: Learn the art of making pasta dough and gnocci. A dedicated chef will walk you through all of the steps in rolling pasta, using a pasta maker, making several types of noodles and gnocci. You will learn secrets of the trade in preparing sauces and most importantly, enjoy a glass of wine and dine on your own cooked pasta dishes.
  • Oct. 21 | Belvedere Mixology Class: Enjoy this special class hosted by Belvedere Vodka during the annual Middleburg Film Festival. Belvedere’s very own mixologist will conduct a seminar on how to create specialty, seasonal cocktails using Belvedere.
  • Oct. 28 | Champagne Cocktails & Caviar Nightmares: Champagne and caviar unite for a scary good combination! Enjoy a special tasting class featuring some of the world’s finest champagnes and learn how it is made, the difference between vintage and non-vintage, and why it pairs perfectly with caviar. After the tasting, Salamander’s staff will mix up some of their favorite sparkling cocktails for you to recreate at home.

Three Fox Vineyards Middleburg VA17. Race through Tuscany 5K and 1-Mile Run at Three Fox Vineyards: Oct. 8

5k “Race through Tuscany” is back! Hosted this year by Travis Bishop of Bishops Events, this 5k is a race through the vineyard and rolling hills of Three Fox. The 5K race begins at 9 a.m., the 1-Miler starts at 9:05 a.m. and complimentary tastings and discounts await you at the finish line. Sign up here.

Also, Casey Cline will be playing from 1:30-4:30 p.m.

18. “One Second of Grace” at Trillium Farm: Oct. 8

A Place to Be presents “One Second of Grace,” a new musical composed by Tom Sweitzer and Kyle Boardman.

The story revolves around a high school assignment asking each student to take a picture of the most meaningful second of their lives. Through painful personal struggles and normal everyday confusion, each teenager searches for that second. They begin to realize no matter how tough getting through life can be, every second holds the possibility for beauty.

Tickets will be handed out at the door. Please arrive 15-30 minutes prior to the show to secure a spot. Trillium Farm has a seating capacity of 140 — therefore, seats are limited! Shows at 3 p.m. and 7 p.m.

For more information, visit or call 540-687-6740.

Greenhill Winery Vineyards Middleburg VA yoga19. Vineyasa at Greenhill Winery & Vineyards: Oct. 8 & 22 | 10-11:30 a.m.

Join Amy Rizzotto, owner and founder at Move Well DC and Yoga Heights, at Greenhill Winery for an hour of yoga, plus breakfast and mimosas.

20. Yin Yoga & Yoga Nidra Workshop at Salamander Resort & Spa: Oct. 8 | 10-11:30 a.m.

Rest, destress and manifest. Take a moment to set your seasonal intentions. You’ll start with journaling exercises and guided Pranayama (breath work). Next, you’ll take slow stretching shapes to open channels in the body using meridians and Yin Yoga. You’ll end the class by settling into our body with Yoga Nidra; a guided meditation which directs awareness to different parts of the body. 15 minutes of Yoga Nidra equals one hour of REM sleep! Students may wear socks and bring a notepad. $45 per person; 90 minute class.

For reservations, please call 540-326-4060.

National Sporting Library and Museum Middleburg VA21. Sunday Sketch at the National Sporting Library & Museum: Oct. 8 | 2-4 p.m.

Enjoy a free sketching session in the museum galleries! Supplies (pencils, paper, sketch boards, and clipboards) will be provided for attendees. This week’s featured artist is local artist and instructor Mary Jennings.

Please register to Anne Marie Barnes at or 540-687-6542 ext. 25.

22. Admission Open House at Foxcroft School: Oct. 9 | 8:30 a.m.-noon

Families looking for an outstanding secondary school experience for their daughters are invited to visit Foxcroft School.

The open house will feature a “faculty fair” so visitors can meet and speak with teachers and administrators about Foxcroft’s unique programs. There are also separate student panels for prospective students and their parents to gain personal insight into Foxcroft’s wonderful community. Tours of the campus and opportunities to get an authentic feel for the school by attending classes and “Morning Meeting” round out the program.

To register for an open house, visit or call 540-687-4340. Space is limited; early registration is recommended. Prospective families are also welcome to schedule visits at other times, by calling 540-687-4340 or emailing

23. October Biz Buzz at Side Saddle Cafe: Oct. 10 | 5:30-7:30 p.m.

The Middleburg Business and Professional Association invites you to our October mixer. Members free, non-members $10. We’ll have a 10-minute Biz Buzz to bring you up-to-date. Please RSVP via Facebook or e-mail to

24. Turnout with Rita Mae Brown at the National Sporting Library & Museum: Oct. 10 | 6-7:30 p.m.

Celebrate thousands of years of equestrian attire with author and Master of Foxhounds Dr. Rita Mae Brown! Explore how riders from ancient Greece through modern day dressed for the field.

$5 admission, free to NSLM members. RSVP to Anne Marie Barnes at or 540-687-6542 ext. 25.

25. Hill School Golf Open at Bull Run Golf Club: Oct. 11

Join the Hill School Alumni Association, sponsor, and your friends supporting need-based financial aid at Hill School, benefitting children from all walks of life throughout our community! Improve your game, have fun, win a 50/50 raffle and prizes, and more!

New for 2017:

  • A lower rate at $125 for individual player, includes box lunch, buffet dinner, short game clinic, prizes;
  • One hour of short game clinic, 30 minutes for chipping and 30 minutes for putting, at 10:30 a.m. before the noon start, included for registered players;
  • $50 Mulligan, Lifeline, 50/50 Raffle Package lets you use a Pro’s drive on two holes, three mulligans, plus a 50/50 raffle ticket.
  • Online convenience, sign up and pay for everything online.
  • All this, plus on-course prizes for longest drive men/women, closest to the pin men/women, and more.

26. Conversations in History – A Fresh Look at the Frank Wanzer Escape at Mt. Zion Historic Park: October 12 | 7-8:30 p.m.

On Christmas Eve 1855, Frank Wanzer and five other individuals escaped from a farm near Aldie, risking their lives for a chance at freedom. The story became incredibly popular after William Still recounted it in his 1872 book covering stories from the Underground Railroad.

So what happened in one of America’s most famous slave escapes, which began in the Mosby Heritage Area? Join NOVA Parks and the Mosby Heritage Area Association for the final installment of the 2017 “Conversations in History” series as they welcome historian Deborah Brower. Brower will explore this sensational episode in Northern Virginia’s history with new research and a fresh eye.

Cost for the program is $10 for adults and $5 for students. Tickets can be purchased at the door. Please dress for the weather.

27. Virginia Fall Races at Glenwood Park: Oct. 14

Join us to celebrate the 63rd running of the Virginia Fall Races! The Theodora A. Randolph Hunter Field Championship Finals begin at 9 a.m. Race post time is 1 p.m. This event benefits the Inova Loudoun Healthcare Foundation and the Glenwood Park Trust.

28. Harvest Festival at Three Fox Vineyards: Oct. 14

Come to Three Fox and enjoy a hayride and lots of fall fun! Roast hot dogs and marshmallows. Pamela Anderson will have Stella & Dot jewelry, Jordan Sullivan, an independent consultant for LuLaRoe, will be there, and Carly Prow will be representing Rodan & Fields skincare!

Salamander Resort Middleburg VA29. Raid the Cellar at Salamander Resort & Spa: Oct. 14 | 10 a.m.-5 p.m.

Stop by Salamander Resort & Spa’s pop-up wine shop and stock up your wine cellar! Just in time for the holidays, you will be able to purchase exclusive selections of their rare and hard to find wines as well as sample a wide selection of domestic and internally wines.

For more information, please call 540-326-4070.

30. Advanced Ashtanga Yoga Workshop at Salamander Resort & Spa: Oct. 14 | Noon- 1:45 p.m.

The Ashtanga Yoga Sequence is a time-honored, challenging and life-changing yoga practice. Ashtanga Yoga uses a set Vinyasa sequence that is the same every time you practice. Often known as “Complete Fitness Yoga” or “Householder Yoga,” the Ashtanga Yoga Method was designed to try and fit everything you need into a condensed, efficient and effective practice. Note: this is an intermediate to advanced level practice. One hour and 45 minute class. $35 per person.

For reservations, please call 540-326-4060.

31. Heritage Breed Wine Dinner at Ayrshire Farm: Oct. 14 | 6-10 p.m.

Enjoy a night of fine food and wine at Ayrshire Farm! The evening starts with a cocktail hour with passed hors d’oeuvres and a heritage breed butcher demonstration. Next comes a 4-course plated dinner featuring Ayrshire Farm heritage breed meats prepared by Ayrshire Executive Chef Lawrence Kocurek paired with wine selections and discussion from Sarah Walsh of Country Vintner. $125 per person (includes tax & gratuity).

32. “A Will to Survive” at Loudoun County High School: Oct. 16

The Same Sky Project presents “A Will to Survive,” a rock opera about suicide prevention, mental health and finding hope while being a teenager today. One show only! Free admission. Starts at 7 p.m.

For more information, visit or call 540-687-6740.

33. Middleburg Film Festival: Oct. 19-22

The Middleburg Film Festival offers four days of fantastic films in a spectacular setting. A carefully curated selection of narrative and documentary films screen in intimate theatre environments, followed by fascinating Q and A’s with world-renowned filmmakers, actors, and other special guests. The films include festival favorites, world premieres, first-class foreign films and Academy Award contenders.

Find out more about the festival and purchase tickets at

34. The Perfect Date at Salamander Resort & Spa: Oct. 19-22

Whether it is a first or 100th, we have a movie-worthy day date just for you! Rent Salamander’s new exclusive Shinola bicycles and take off on an adventure through Virginia’s horse and wine country. Come to a stop at a local vineyard, and indulge in Executive Chef Ryan Arensdorf’s curated Luxury Vineyard Dining picnic with a local cheese and charcuterie board, country-style pate with housemade cherry mostarda, smoked salmon tartar, royal osetra caviar with traditional accompaniments, a bottle of Greenhill Winery‘s Blanc de Blanc and much more. $320 for two people.

For reservations, please call 540-326-4020.

Salamander Resort and Spa Middleburg VA35. Red Carpet Ready at Salamander Resort & Spa: Oct. 19-22

Prepare for the flashing lights and get a youthful glow at Salamander Spa. Receive an Elemis BioTec Firm-a-Lift or BioTec Line Eraser Facial and receive a complimentary Gift of BioTec travel size cleanser and moisturizer. 110 minutes, $210 per person.

For reservations, please call 540-326-4055.

36. Ride Off into the Sunset at Salamander Resort & Spa: Oct. 19-22

Have your true fairytale ending with a Sunset Trail Ride for two, followed by an evening of sweeping countryside views, paired with a local bottle of wine. $690 per couple.

For reservations, please call 540-326-4085.

37. The Butterfly 5K/10K to benefit Blue Ridge Hospice: Oct. 21

We invite you to participate in The Butterfly 5K/10K to benefit Blue Ridge Hospice!

Join us Oct. 21 to honor those we’ve lost and raise awareness and funds for patients and families. Whether you’re a runner or walker, you can take part in this event!

The 5K is a gorgeous walk or run through lush Virginia country … mountain views, beautiful scenery and a variety of tree species at the VA State Arboretum. On the 10K course, you’ll run through the arboretum, on through a barn, by grazing horses and around an historic plantation estate!

Your efforts will help Blue Ridge Hospice, a not-for-profit healthcare organization, continue with the mission of never turning anyone away based on financial ability. Your walk or run will give others the gift of comfort, compassion and dignity in their last months, weeks and days.

Race day registration will close at 8:45 a.m. 10K Runners will begin the race at 9 a.m., 5K walkers/runners will begin at 9:10 a.m.

38. Livin’ la Dolce Vita at Three Fox Vineyards: Oct. 21 | 8 a.m.-5 p.m.

Spend a day with Three Fox experiencing la dolce vita! Enjoy a picnic in their meadow (complete with a nap in one of their creek-side hammocks), play bocce ball or corn hole in the vineyard, sit at one of their hillside tables, on their tented al fresco terazza, or their brick patio and take in the view while you enjoy their wines, which are made in the old world tradition.

39. Legends by Lanternlight – Remembrances of Brentsville at Brentsville Courthouse Historic Centre: Oct. 21 | 7:30-9:30 p.m.

Hear the stories of Brentsville from the perspective of the people who lived and passed through here during the Civil War. The program will be led by the costumed interpreters of the Mosby Heritage Area Interpretive Group. The county seat for Prince William County during the Civil War, Brentsville saw soldiers passing through it throughout much of the Civil War. Confederates used the village as a point of mustering point at the beginning of the war before Union soldiers occupied the area from 1862-1865. The community even witnessed a few minor, but deadly battles. Come learn these stories and more as part of a lantern-lit tour of this historic village.

Walking is required. Please dress appropriately. This program is free!

For questions, please call 540-687-5188 or 703-365-7895.

40. “Horsemanship in Ancient Greece” at the National Sporting Library & Museum: Oct. 26 | 6-7:30 p.m.

Join us at NSLM as George Mason University art history professor emerita Carol C. Mattusch compares modern riding, tack and philosophy with that of the ancient Greeks. $5 admission, free to NSLM members. Please RSVP to Anne Marie Barnes at or 540-687-6542 ext. 25.

Empower Adventures Pumpkin Drop Middleburg VA41. Halloween Celebration at Three Fox Vineyards: Oct. 27-29

Discounts for everyone in costume and their Haunted Trail will be open again! Enjoy live music on Saturday by Movin’ On from 1:30-4:30 p.m.! Stay later, they’re open ’til 7 p.m. this Saturday! On Sunday, enjoy live music byBig Steve and Pete from 1:30-4:30 p.m.!

42. 868 Vineyards Wine Dinner at Salamander Resort & Spa: Oct. 27 | 6:30-10:00 p.m.

Enjoy an exclusive four-course dinner prepared by Executive Chef Ryan Arensdorf and paired perfectly with selections from local vineyards in Salamander’s intimate, private dining room at Harrimans. $150 per person. For reservations, please call 540-326-4070.

43. International Gold Cup at Great Meadow: Oct. 28

The legendary annual Virginia Gold Cup steeplechasing classic is now run before a sellout crowd of over 50,000 people. Race day activities include terrier races, shopping, hat contests, tailgate contests, and some of the best steeplechase racing you’ll find anywhere.

44. Murder Mystery Show – The Hamilton Murders at Salamander Resort & Spa: Oct. 29

On July 11, 1804, Alexander Hamilton lies dying on the ground. Aaron Burr stands nearby, a smoking gun in his hand. Historians have told their side of the story but join us and hear the untold version. Decide who the real killer is and prepare to change the course of history! Starts at 11:30 a.m. Lunch is served at 12:30 p.m. $85 per person. For reservations please call 540-326-4070.

Salamander Resort Yappy Hour Halloween Middleburg VA45. Yappy Hour Costume Contest at Salamander Resort & Spa: Oct. 31 | 5-7 p.m.

Treat your dog and yourself to a special Yappy Hour on Halloween! Dress your pup to impress for a paw-some costume contest and enjoy a special menu from Gold Cup Wine Bar featuring Sharing Chow including Salamander’s Pimento Cheese “Hush Puppies” and a refreshing Pup-tail Menu with their Spicy Pup-arita with Blanco tequila. A portion of the proceeds are donated to the Middleburg Humane Foundation. Dogs must remain on a leash at all times. Weather dependent.

46. Hot Dog! It’s Halloween! at the Middleburg Community Center: Oct. 31 | 5:30-7:30 p.m.

Come in your best costume for the annual MCC “Hot Dog, It’s Halloween!” Hot dog dinner will be provided, as well as goodie bags for the kiddos. Entry is free, bring your friends and get ready to have a spooktacular time!

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