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Ultimate 14-Day Charlottesville and Blue Ridge Parkway Road Trip Itinerary
Last updated: 2024 Jun 14Welcome to Charlottesville
Morning
Start your journey with a delightful breakfast at Bodo's Bagels, a local favorite known for its fresh bagels. Afterward, immerse yourself in history with the Charlottesville Ghosts of Court Square Walking Tour, where you'll learn about the city's spooky past.
Afternoon
For lunch, head to The Virginian Restaurant, a Charlottesville institution since 1923. Afterward, explore the University of Virginia, a UNESCO World Heritage Site, and take a stroll through the historic Grounds.
Evening
Enjoy a relaxing dinner at Revolutionary Soup, known for its delicious soups and sandwiches. End your day with a leisurely walk on the Downtown Mall, a vibrant pedestrian street with shops, restaurants, and entertainment.
Bedtime
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3.00Charlottesville Ghosts of Court Square Walking Tour
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3.00Charlottesville Ghosts of Court Square Walking Tour
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University of Virginia
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University of Virginia
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Vineyards and History
Morning
Start your day with a scenic drive to Blenheim Vineyards, owned by musician Dave Matthews. Enjoy a wine tasting and take in the beautiful views of the surrounding vineyards.
Afternoon
For lunch, visit Christian's Pizza, a local pizzeria known for its New York-style pies. Afterward, explore the Michie Tavern, a historic 18th-century tavern where you can experience colonial-era dining.
Evening
End your day with a visit to Mulberry Row at Monticello, the former plantation of Thomas Jefferson. Take a guided tour to learn about the lives of the enslaved individuals who lived and worked on the estate.
Bedtime
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5.00Blenheim Vineyards
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5.00Blenheim Vineyards
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4.82Michie Tavern
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4.82Michie Tavern
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Mountain Majesty
Morning
Enjoy a hearty breakfast at Littlejohn's New York Deli, known for its classic deli sandwiches. Then, embark on a day trip to Shenandoah National Park, where you can drive along the scenic Skyline Drive and take in the breathtaking views of the Blue Ridge Mountains.
Afternoon
Pack a picnic lunch and stop at one of the park's many overlooks to enjoy the scenery. You may also want to take a short hike to a waterfall or explore one of the park's visitor centers.
Evening
Return to Charlottesville in the evening and dine at C&O Restaurant, a fine dining establishment housed in a historic train station. Afterward, relax with a cocktail at The Alley Light, a speakeasy-style bar known for its craft cocktails.
Bedtime
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4.06Shenandoah National Park
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4.06Shenandoah National Park
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Wine and Dine
Morning
Start your day with a visit to Jefferson Vineyards, one of the oldest wineries in Virginia. Enjoy a wine tasting and learn about the history of winemaking in the region.
Afternoon
For lunch, head to Mas Tapas, a Spanish restaurant known for its small plates and lively atmosphere. Afterward, visit Trump Winery, owned by the Trump family, for a tour and tasting.
Evening
Enjoy a sophisticated dinner at Duner's Restaurant, a farm-to-table restaurant known for its seasonal menu. Afterward, take a leisurely stroll through the gardens at the University of Virginia's Morven Gardens.
Bedtime
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Jefferson Vineyards
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Jefferson Vineyards
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Trump Winery
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Trump Winery
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Culinary Delights
Morning
Indulge in a leisurely breakfast at Fleurie Restaurant, a French bistro known for its elegant cuisine. Afterward, take a Charlottesville Scavenger Hunt to discover hidden gems and local landmarks.
Afternoon
For lunch, try the famous sandwiches at Subway, a popular chain known for its customizable subs. Afterward, visit the Charlottesville Historic Downtown Mall, a pedestrian mall with shops, restaurants, and entertainment venues.
Evening
Dine at The Local, a farm-to-table restaurant known for its seasonal menu and locally sourced ingredients. Afterward, catch a show at the The Paramount Theater, a historic venue that hosts a variety of performances.
Bedtime
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Charlottesville Scavenger Hunt
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Charlottesville Scavenger Hunt
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4.44Charlottesville Historic Downtown Mall
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4.44Charlottesville Historic Downtown Mall
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Outdoor Adventures
Morning
Start your day with a hike in the Rivanna Trail, a 20-mile loop trail that encircles Charlottesville. Enjoy the natural beauty of the area and keep an eye out for wildlife.
Afternoon
For lunch, enjoy a picnic at Darden Towe Park, a scenic park with views of the Rivanna River. Afterward, rent a kayak or paddleboard and explore the river on the water.
Evening
Dine at Tavola, an Italian restaurant known for its handmade pasta and wood-fired pizzas. Afterward, take a leisurely walk along the Rivanna River and enjoy the sunset.
Bedtime
Find amazing hotels in Charlottesville, Virginia.
Historic Sites and Local Flavors
Morning
Start your day with a visit to Monticello, the historic home of Thomas Jefferson. Take a guided tour of the house and gardens and learn about the life and legacy of the third president of the United States.
Afternoon
For lunch, head to The Whiskey Jar, a Southern restaurant known for its comfort food and extensive whiskey selection. Afterward, visit the Charlottesville Historic Downtown Mall for shopping and entertainment.
Evening
Dine at The Alley Light, a speakeasy-style bar known for its craft cocktails and small plates. Afterward, enjoy a live music performance at The Jefferson Theater, a historic venue that hosts a variety of concerts and events.
Bedtime
Find amazing hotels in Charlottesville, Virginia.
4.44Charlottesville Historic Downtown Mall
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4.44Charlottesville Historic Downtown Mall
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4.70The Jefferson Theater
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4.70The Jefferson Theater
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Local Markets and Art Galleries
Morning
Start your day with a visit to the Charlottesville City Market, a vibrant farmers' market that offers fresh produce, baked goods, and artisanal products. Afterward, explore the McGuffey Art Center, a community art center with galleries and studios.
Afternoon
For lunch, try the famous burgers at Miller's Downtown, a local bar known for its casual atmosphere and live music. Afterward, visit the Kluge-Ruhe Aboriginal Art Collection, the only museum in the United States dedicated to Australian Aboriginal art.
Evening
Dine at The Local, a farm-to-table restaurant known for its seasonal menu and locally sourced ingredients. Afterward, take a leisurely walk through the Charlottesville Historic Downtown Mall and enjoy the street performers and outdoor cafes.
Bedtime
Find amazing hotels in Charlottesville, Virginia.
4.44Charlottesville Historic Downtown Mall
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4.44Charlottesville Historic Downtown Mall
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Gardens and Galleries
Morning
Start your day with a visit to the Ash Lawn-Highland, the historic home of James Monroe. Take a guided tour of the house and gardens and learn about the life and legacy of the fifth president of the United States.
Afternoon
For lunch, head to The Whiskey Jar, a Southern restaurant known for its comfort food and extensive whiskey selection. Afterward, visit the Charlottesville Historic Downtown Mall for shopping and entertainment.
Evening
Dine at The Alley Light, a speakeasy-style bar known for its craft cocktails and small plates. Afterward, enjoy a live music performance at The Jefferson Theater, a historic venue that hosts a variety of concerts and events.
Bedtime
Find amazing hotels in Charlottesville, Virginia.
4.44Charlottesville Historic Downtown Mall
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4.44Charlottesville Historic Downtown Mall
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4.70The Jefferson Theater
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4.70The Jefferson Theater
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Historic Sites and Local Flavors
Morning
Start your day with a visit to Monticello, the historic home of Thomas Jefferson. Take a guided tour of the house and gardens and learn about the life and legacy of the third president of the United States.
Afternoon
For lunch, head to The Whiskey Jar, a Southern restaurant known for its comfort food and extensive whiskey selection. Afterward, visit the Charlottesville Historic Downtown Mall for shopping and entertainment.
Evening
Dine at The Alley Light, a speakeasy-style bar known for its craft cocktails and small plates. Afterward, enjoy a live music performance at The Jefferson Theater, a historic venue that hosts a variety of concerts and events.
Bedtime
Find amazing hotels in Charlottesville, Virginia.
4.44Charlottesville Historic Downtown Mall
Book Now
4.44Charlottesville Historic Downtown Mall
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4.70The Jefferson Theater
Book Now
4.70The Jefferson Theater
Book Now
Local Markets and Art Galleries
Morning
Start your day with a visit to the Charlottesville City Market, a vibrant farmers' market that offers fresh produce, baked goods, and artisanal products. Afterward, explore the McGuffey Art Center, a community art center with galleries and studios.
Afternoon
For lunch, try the famous burgers at Miller's Downtown, a local bar known for its casual atmosphere and live music. Afterward, visit the Kluge-Ruhe Aboriginal Art Collection, the only museum in the United States dedicated to Australian Aboriginal art.
Evening
Dine at The Local, a farm-to-table restaurant known for its seasonal menu and locally sourced ingredients. Afterward, take a leisurely walk through the Charlottesville Historic Downtown Mall and enjoy the street performers and outdoor cafes.
Bedtime
Find amazing hotels in Charlottesville, Virginia.
4.44Charlottesville Historic Downtown Mall
Book Now
4.44Charlottesville Historic Downtown Mall
Book Now
Gardens and Galleries
Morning
Start your day with a visit to the Ash Lawn-Highland, the historic home of James Monroe. Take a guided tour of the house and gardens and learn about the life and legacy of the fifth president of the United States.
Afternoon
For lunch, head to The Whiskey Jar, a Southern restaurant known for its comfort food and extensive whiskey selection. Afterward, visit the Charlottesville Historic Downtown Mall for shopping and entertainment.
Evening
Dine at The Alley Light, a speakeasy-style bar known for its craft cocktails and small plates. Afterward, enjoy a live music performance at The Jefferson Theater, a historic venue that hosts a variety of concerts and events.
Bedtime
Find amazing hotels in Charlottesville, Virginia.
4.44Charlottesville Historic Downtown Mall
Book Now
4.44Charlottesville Historic Downtown Mall
Book Now
4.70The Jefferson Theater
Book Now
4.70The Jefferson Theater
Book Now
Historic Sites and Local Flavors
Morning
Start your day with a visit to Monticello, the historic home of Thomas Jefferson. Take a guided tour of the house and gardens and learn about the life and legacy of the third president of the United States.
Afternoon
For lunch, head to The Whiskey Jar, a Southern restaurant known for its comfort food and extensive whiskey selection. Afterward, visit the Charlottesville Historic Downtown Mall for shopping and entertainment.
Evening
Dine at The Alley Light, a speakeasy-style bar known for its craft cocktails and small plates. Afterward, enjoy a live music performance at The Jefferson Theater, a historic venue that hosts a variety of concerts and events.
Bedtime
Find amazing hotels in Charlottesville, Virginia.
4.44Charlottesville Historic Downtown Mall
Book Now
4.44Charlottesville Historic Downtown Mall
Book Now
4.70The Jefferson Theater
Book Now
4.70The Jefferson Theater
Book Now
Local Markets and Art Galleries
Morning
Start your day with a visit to the Charlottesville City Market, a vibrant farmers' market that offers fresh produce, baked goods, and artisanal products. Afterward, explore the McGuffey Art Center, a community art center with galleries and studios.
Afternoon
For lunch, try the famous burgers at Miller's Downtown, a local bar known for its casual atmosphere and live music. Afterward, visit the Kluge-Ruhe Aboriginal Art Collection, the only museum in the United States dedicated to Australian Aboriginal art.
Evening
Dine at The Local, a farm-to-table restaurant known for its seasonal menu and locally sourced ingredients. Afterward, take a leisurely walk through the Charlottesville Historic Downtown Mall and enjoy the street performers and outdoor cafes.
Bedtime
Find amazing hotels in Charlottesville, Virginia.
4.44Charlottesville Historic Downtown Mall
Book Now
4.44Charlottesville Historic Downtown Mall
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