I’m back from my whirlwind week in Charlottesville, Virginia and I feel like I’m still recovering. The first 36 Hours in Charlottesville Wine Country were jam packed with chef’s tasting meals and wine tastings in beautiful bucolic settings. I’m recapping this part of my trip here and will put together a travel guide to Charlottesville in another post.

While I have returned, you could be headed to Charlottesville soon if you win the 36 Hours in Charlottesville contest. The giveaway includes: Pippin Hill Vintner’s Table for Two, Early Mountain Gift Certificate for $150, The Clifton complimentary one night stay for two, Red Pump Kitchen Gift Certificate for $100, and Market at Grelen Gift Certificate for $50. You can refer to the terms and conditions for restrictions and more information.

After we arrived in Charlottesville, we checked into The Clifton Inn which is a 20 room boutique hotel set on 100 acres of Virginia countryside that just recently underwent a renovation by the Blackberry Farm Design team. It’s now a a mix of classic and contemporary style to create a chic and modern country house feel. Fun fact, it was originally constructed in 1799 as a classic colonial-style home for Thomas Jefferson’s daughter Martha Jefferson and her husband Thomas Mann Randolph.

I’m not sure I’ll ever go back to Napa since the flight to Charlottesville from New York is only an hour long. It’s a really easy weekend trip from Virginia and Washington, DC too.

I loved the wallpaper and paint combination in the main floor powder room.

If you don’t stay at The Clifton Inn, you can still enjoy a meal in their chic 1799 Restaurant helmed by Michelin-starred Executive Chef Matthew Bousquet or have a drink in the Copper Bar.

Breakfast is served on the enclosed patio.

I had a corner suite with a sitting room and separate bedroom.

My bathroom included this lovely claw foot tub, a separate shower, double sinks and a vanity. I loved the wall color here too.

This is the honeymoon cottage behind the main house.

You walk down the driveway to access the pool at The Clifton Inn. We only stayed one night but I thought it was a lovely place to stay and would love to spend more time there on a future trip.

Our first wine stop was to Pippin Hill Farm & Vineyards which was on the recommendation list of everyone who reached out about my trip to Charlottesville.

When we arrived, it was foggy and grey but luckily the clouds parted and the sun came out.

They were setting up for an event in this main building but there are lot of indoor and outdoor places for dining and wine tastings.

The decor was very charming and perfect for the rustic setting.

Before sitting down to eat, we were treated to a tour of the farm by certified horticulturist Diane Burns.

The view at Pippin Hill after the sun came out.

Unlike Napa, Charlottesville Wine Country is as much about food as it is wine. I find traditional wine tastings incredibly boring but here you can enjoy a meal with suggested wine pairings. It also makes the Charlottesville vineyards a great family destination and not just a place for adults.

Another look at Pippin Hill.

You can experience wine tastings inside and out at Pippin Hill.

After our tour of the farm, we sat down a meal with wine pairings at the Vintner’s Table.

The table was set with flowers from the farm.

The menu at the Vintner’s Table. Everything was delicious!

The gazpacho.

The entrance to Pippin Hill is lined with lush Limelight hydrangea hedges for a dramatic introduction to the property.

Later in the day, we headed to the Downtown Mall in Charlottesville to the Red Pump Kitchen for dinner.

Red Pump is very popular so I would make a reservation early. I would also request to sit at one of the low tables. The high table we sat at in the front window was extremely uncomfortable.

The chef’s tasting menu from our dinner at Red Pump. I’m on a cleanse diet now this week.

We passed lots of horse farms and rolling hills on the drive from The Clifton to The Market on Grelen on Wednesday via Monticello Wine Tour and Coach. I bet it will be even more beautiful when the leaves have changed and it’s full of autumn colors.

The Market at Grelen includes many things such as, a European style garden shop, a casual farm to table cafe, pick your own orchards, wine tastings, a wedding venue, and hiking trails set on a 600 acre nursery.

I loved all the pretty heirloom pumpkins when we arrived.

The garden shop is full of gardening accessories, gift items, holiday decorations, and more.

We took a little trek up to the top of the property to admire the view.

Many couples get married at the top of this hill.

Owners Leslie and Dan Gregg talking about the property.

Another view of the property on the way to the apple orchard.

We did a little apple picking of our own on the tour of the property.

The apple orchard.

Once back at The Market at Grelen, we had a little wine tasting.

We ended our 36 Hours in Charlottesville Wine Country at the Early Mountain Vineyards.

We started off with a wine tasting upstairs at Early Mountain Vineyards.

Early Mountain Vineyards was the most traditional of all the places we visited on this trip

A map of Virginia wine country.

The tasting area at Early Mountain after which we took a tour of the property.

After the property tour, we sat down to lunch at a very chicly decorated table.

You get the idea of how beautiful events and weddings must be at Early Mountain.

The “Virginia Table” tasting menu and wine pairings.

The motto of the state is “Virginia is for Lovers” but they could change it to “Virginia is for Wine Lovers” after this trip. I had a great time learning more about this area during my 36 Hours in Charlottesville Wine Country trip and I can’t wait to return. Don’t forget to enter the contest so you can try for a chance at your own trip.

All photos by Heather Clawson for Habitually Chic.