Travel
Virginia Hunt Country Packing List
October 31st, 2025
We’re all about helping you look your best, wherever you are in the world. Here’s what to pack for a trip to Virginia Hunt Country, according to Tuckernuck co-founder, Maddy Grayson.
Meet Our Expert: Maddy Grayson
Maddy grew up in Washington, D.C. and has been visiting Virginia’s Hunt Country—Upperville, The Plains, Marshall, and Middleburg—for decades. She frequents Upperville with her family.
Hunt Country Style, Explained
The Local Style: Equestrian at its core and rich in heritage, the look is practical yet polished. Effortless, functional, and made for outdoor living—no heels needed.
Fashion Fundamentals: Jeans, riding boots, and wellies, layered with luxe cashmere, romantic florals, waxed jackets, and classic shirting. Just timeless pieces made for crisp days in the field and charming strolls through town.
What to Pack for Hunt Country
From dressy to casual—these are 31 pieces you’ll wear throughout your stay.
DRESSES
Sweater Dress
Shirt Dress
Day Dress
TOPS
White Blouse
Casual Button-Down
Cashmere Sweater
Fisherman Sweater
OUTERWEAR
Barbour Jacket
Field Jacket, Barn Coat, or Waxed Cotton Jacket
Packable Raincoat or Poncho
Lightweight Quilted Vest
Tweed Blazer
Fleece Pullover
BOTTOMS
Casual Denim
Dressy Denim
Corduroy Pants
Riding Leggings
Athletic Pants or Leggings
Suede Skirt
FOOTWEAR
Hiking Shoes
Waterproof Boots or Wellies
Riding Boots
Heeled Boots
Suede Loafers
ACCESSORIES
Tack Hat
Silk Scarf
Suede Belt
Tote Bag
Crossbody Bag
Chandelier Earrings
Sunglasses
Our Top 4 Packing Tips
Pack Layers
Hiking, fishing, kayaking, canoeing—be practical and prepared for adventure.
Leave Your Heels at Home
Nobody wears heels. If you want to dress up for dinner, do a chunkier heeled boot.
Bring Extra Clothes
Don’t be afraid to get dirty! If you’re horseback riding or hiking, plan on changing after.
Don't Forget Socks
Tall, thick socks are a must for hiking and riding.
Let us help you dress like a local.
Fall Horse Race
Channel equestrian style in materials like herringbone and tweed, then accessorize with heritage-inspired accessories like riding boots and a tack hat.
Hiking
Get out and explore! It’s cooler in the mornings, mountains, and shade so layer up in a tee, pullover, and Barbour jacket.
Antiquing
Keep it classic for a day in town—think denim, cashmere, and shoes that are made for walking. And, of course, bring a big tote to carry all your finds!
Apple Picking
This is a family activity so comfort is key. Dress in leggings and boots so you can reach and bend over easily, but add a cable knit sweater on top for a look that’s photo-worthy.
Wine Tasting
Ditsy floral feels at home at the vineyard. Accessorize with a cropped suede jacket, boots, and a western belt.
Dinner
Dress up your riding boots with an equestrian-inspired top. Black accessories elevate the look for nighttime!
FAQs
Why do we love Virginia Hunt Country?
Virginia Hunt Country—Upperville, The Plains, Marshall, and Middleburg—is a timeless escape where you instantly unwind. Just a short drive from Washington, D.C., it draws visitors from across the country, all united by a love of nature and horses. Rolling hills, fresh air, and endless trails set the scene for hiking, fishing, and apple picking, while charming towns and storied homes bring the region’s heritage to life.
When is the best time to visit Virginia Hunt Country?
It depends on the trip and weather you want! Summer is nice because you can visit local vineyards and sit outside, while fall is the quintessential time for apple picking and leaf peeping. Middleburg hosts two horses races a year, in April and October, so that’s another popular time to go, especially for those local to the area.
What is the weather like in Virginia Hunt Country?
Hunt Country experiences all four seasons: hot, humid summers; mild autumns; cold winters; and warmer springs. July is typically the hottest month, while January is the coldest. In the mountains, the air is cooler and less humid, averaging about 10 degrees lower year-round.
What to pack for men visiting Virginia Hunt Country?
Use this woman’s packing list as a guide! He’ll still want to pack for outdoor adventures—hiking gear, layers, and a Barbour jacket are a must.
What is a packing list?
A packing list is a tool that helps ensure you have everything that you need packed and ready for your destination. Let us help you plan your outfits and simplify your packing.
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