Packing List: Middleburg, VA
What to Pack for 3 Days in Middleburg, Virginia (June Edition)
If you're heading to Middleburg in June, expect warm afternoons, cooler mornings, and the occasional summer thunderstorm. Daytime temperatures typically hover in the low 80s, while mornings and evenings can dip into the low 60s.
Whether you're spending your days horseback riding, wine tasting, exploring the countryside, or lounging by the pool at Salamander, here's exactly what I'd pack for a long weekend.
Clothing
3 Daytime Outfits
Think easy, polished, and comfortable.
Linen dress
Matching set
Relaxed trousers and a lightweight top
Comfortable flats / sandals
Middleburg is horse country chic at its finest. You'll fit right in with natural fabrics, classic silhouettes, and effortless pieces that feel elevated without trying too hard.
2 Dinner Outfits
Evenings feel slightly dressier than you might expect.
Midi dress
Lightweight sweater for layering
Block heels or dressy flats
Classic jewelry
Pool Essentials
If you're staying at Salamander, you'll want dedicated pool attire.
2 swimsuits
Cover-up
Wide-brim hat
Sunglasses
SPF
Layers
Lightweight cardigan
Denim jacket or linen blazer
Early mornings on the property can feel surprisingly cool before the Virginia sun warms things up.
Shoes
You don't need many, but choose wisely.
Comfortable walking shoes
Sandals
Dinner shoes
The town is walkable, but you'll likely spend time exploring wineries, gardens, trails, and gravel paths.
Accessories
Crossbody bag
Camera
Portable charger
Reusable water bottle
Umbrella or lightweight rain jacket
June averages more than two inches of rainfall and afternoon showers aren't unusual.
Middleburg has a slower pace than most weekend destinations. The best wardrobe strategy is packing versatile pieces you'll actually want to wear more than once.
What I wore:
I chose a cohesive color palette (navy + silver + brown), and packed minimal outfits that were slightly dressy, slightly casual, and comfortable in breathable fabrics. It might seem repetitive to pack 3 navy dresses, but it worked for me to have this as a set outfit formula, and switch out the dress each day, and switch out the accessories to modify the look.
The sleeper hit was this Muji dress that I got in Japan. It continues to impress me with how versatile it is, and for this trip it functioned as a perfect pool cover up.
Thrifted hat Buy Secondhand on Poshmark
Old straw hat Shop similar
Thrifted heels Shop similar
Basket bag - ethically made
Linjer diamond earrings - ethically made
Linjer diamond necklace - ethically made
Nana’s beaded necklace Shop similar
Thrifted tradlands dress Shop Tradlands dresses - ethically made
Outfit 1: Pool day
Outfit 2: Anniversary dinner
Outfit 3: Travel day outfit
Outfit 4: Vineyard visits
Brands to shop secondhand
I like to dress like me on vacation, but its also fun to tailor your clothes a bit to your destination while still being authentically you. Its not necessary to buy new things for a trip, but if you’re looking to thrift similar looks, these are brands I would be on the lookout for:
Hill House Home
Doen
Christy Dawn
Reformation
Tuckernuck
Ralph Lauren
J.Crew
Jenni Kayne
La Ligne
J.Crew Swim
Margaux
Sezane
Loeffler Randall
Toteme
The Row
Khaite
Faithfull the Brand
Apiece Apart
Staud
Eileen Fisher (especially vintage)
Liz Claiborne vintage linen
Talbots
Brooks Brothers
Mara Hoffman
Ozma of California
Happy travels! xoxo Lauren
