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Guide to Virginia's Monticello Wine Trail
Olivia Kennedy
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Guide to Virginia's Monticello Wine Trail

Essential Tips for survival on the trail.

Of the few places in the country where you’d find a Wine trail, the one at Monticello should easily be up there on your ‘must see’ list. This wine trail boasts of many a top-rated winery in the United States. The Monticello Wine Trail currently consists of 33 of the best wineries in Virginia and is a definite must see if wine is what gets your juices flowing.

History of the Monticello AVA and wine trail

The Monticello AVA is the first established AVA of Virginia. Named after its namesake, the residence of the great Thomas Jefferson, it is situated in Virginia’s Piedmont region along the scenic Blue Ridge Mountains. Winemaking in this region could be traced back by about 250 years! Thomas Jefferson pioneered this cause, providing assistance to the first wine planters in Monticello. The Monticello Wine Trail is regarded as the birthplace of American wines. Established in 1984, it is an association of the best and top rated wine and grape producers of Virginia, all located within a 25-mile radius around Charlottesville. All share their knowledge, experience, and expertise to come up with world-class quality of wines that are exported to even the most notoriously famous wine producing locations around the globe.


Experience The Taste of Monticello Wine Trail Festival.

The wine tasting festival held every year at Monticello is every wine lover’s delight! This 3-day festival gives wine aficionados a chance to explore and enjoy the authentic taste and flavor of each winery part of The Monticello Wine Trail. If food, drinks, award shows, entertainment, vineyard tours and merry-making are what get you excited and enthused, then the Taste of Monticello Wine Trail Festival is a match made in heaven for you!

5 "Don't Miss" Wineries on the Monticello Wine Trail.

While all 33 wineries on the trail are unique in their own right, 5 of them stand out.

  • The Cardinal Wine Point & Winery, renowned for its unique and instantly identifiable blends.
  • First Colony Winery, for its magnanimous 5000 square foot wine tasting room and its pristine Albemarle County location. You'll want to pack a wine picnic basket to enjoy while you linger to enjoy the view.
  • Pollak Vineyards, for their award-winning lines of Chardonnay, Cabernet Franc and Merlot blends.
  • Stinson Vineyards, the trendsetters for incorporating environmental sustainability into this industry and specifically in the Monticello wine trail.
  • Michael Shaps Winery for the low price but highly refined and quality wines and for being the sole bag-in-box wine producer in Virginia.

Wine Trail Route Planner

It is easy to get lost in the sheer magnificence of each and every winery of this iconic Virginia wine trail. To ensure that you do not miss out on some of the must-see locations along your vineyard tour, you’d be well advised to use a route planner. Click to plan your route and pay a visit to the top rated wineries of the Monticello Wine Trail.


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  • Central Virginia Region
AVAMonticello AVA
Wine Trail
  • Monticello Wine Trail
Olivia Kennedy

Olivia KennedyOlivia Kennedy

A bottle of wine, a loaf of bread and a block of delicious cheese, these are a few of my favorite things. Follow me as I explore wine country in search of the best of these.

Other posts by Olivia Kennedy
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Full biography

A bottle of wine, a loaf of bread and a block of delicious cheese, these are a few of my favorite things. Follow me as I explore wine country in search of the best of these.



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