Things to Do near Our Inn in Charlottesville VA

The Inn at Monticello in Charlottesville, Virginia is minutes away from a wide variety of activities and attractions. This diverse area has much to offer in the way of restaurants, theater, shopping, and sports.

Be sure to check our Packages & Specials page for great values on lodging combined with dining and sightseeing opportunities.


Charlottesville Pavilion Fridays After Five Free Concerts and Ticketed Performances
During the spring and summer, the City of Charlottesville sponsors free concerts on Friday evenings at the Pavilion open-air theater on the Historic Downtown Mall. Local musicians play rock, jazz, bluegrass, blues, and other forms of music.

The Charlottesville Pavilion also hosts some great headliner entertainment. Past performers have included Bonnie Raitt, Allison Krause, the late James Brown, B.B. King, Willie Nelson, Bruce Hornsby, Lyle Lovett, Lynyrd Skynyrd, the Neville Brothers, Montgomery Gentry, the B-52’s, and Nickel Creek.

The University of Virginia Culbreth Theater and Old Cabell Hall Performances
The UVA Drama Department and the UVA McIntire Department of Music produce or sponsor many fine theatrical and musical performances every year at the Culbreth Theater or Old Cabell Hall, both located on the University grounds. Ticket prices are nominal, but the caliber of performances is outstanding.

The Paramount Theater
The Paramount Theater, located on the Historic Downtown Mall, is now a premiere venue for the performing arts, hosting entertainers such as Tony Bennett, Randy Newman, the Dublin Philharmonic Orchestra, the Chieftains, the Capitol Steps, and other well-known artists, dancers and actors. The Paramount has also hosted simulcasts of the Metropolitan Opera and season premier parties for the British soap opera Downton Abbey!

Live ArtsTheater
The Live Arts Theater is located on Water Street, just one block from the Historic Downtown Mall. It produces an eclectic mix of live performances, featuring mostly local non-professional actors and actresses. Productions have included “Sweeney Todd,” and “A Little Night Music,” by Stephen Sondheim, and “Lysistrata,” by Aristophanes.

The John Paul Jones Arena at the University of Virginia
The new John Paul Jones arena was named a “Top Ten New Concert Venue” for 2007. A beautiful addition to our area, this magnificent 16,000 seat arena allows Charlottesville to attract some of the most popular entertainers in the world, such as the The Eagles, Paul McCartney, Dave Matthews Band, Rod Stewart, Elton John, Eric Clapton, Cirque de Soleil, Taylor Swift, Fleetwood Mac , and Bruce Springsteen and the E Street Band. The “JPJ,” as it is called, is also home to UVA’s men’s and women’s varsity basketball teams, which proudly play – and often are at the top – in the Atlantic Coast Conference.

Night Life on the Historic Downtown Mall
Did you know that Dave Matthews started his musical career in 1990 while tending bar at Miller’s on the Historic Downtown Mall? Miller’s offers live entertainment several nights a week. Enjoy a burger and a brew while checking out some of Charlottesville’s up-and-coming entertainers. There are literally dozens of venues with live music, showcasing real talent, nearly every night of the week in Charlottesville.

Fellini’s #9, around the corner from Miller’s, is another great spot to enjoy live music and good food.

The Jefferson Theater is an historic venue, built in 1912 as a vaudeville theater. It is now set up for contemporary local and nationally known rock musicians and entertainers.

University of Virginia Sports Events
The University of Virginia fields varsity teams in 11 men’s sports and 12 women’s sports. The teams compete in the Atlantic Coast Conference, one of the premiere collegiate sports leagues in the country. In the last few years, the men’s tennis team, baseball and men’s basketball teams have won national championships or been ranked #1 in the country. Football usually draws crowds in excess of 40,000 for home games.

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When we started here at the inn in 2006 the word “foodie” was not in our vocabulary nor was the phrase “Farm to Table.” Now it is! In fact Esquire Magazine named Virginia “The Food Region of 2014.” Charlottesville is a delight for connoisseurs of superb food and wine. In the Historic Downtown area alone, there are more than 50 great restaurants, some fancy, some not, but all serving delicious fare. From Food and Wine Magazine to Trip Advisor and James Beard award nominations the reviews are amazing.   Jane Black, writer for the Washington Post, visited Charlottesville in May 2008 and wrote “If It Tastes Good, It’s in Charlottesville.” In this article, she said, “Thanks to inventive chefs, a commitment to quality and a local focus, this is one college town with all the makings of a food lover’s destination.”

Here are some of our favorite restaurants for lunch, dinner or drinks:

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Historic Sites

The Inn at Monticello is located near many historic estates in Charlottesville.

The home of Thomas Jefferson is located 2.4 miles from the Inn at Monticello. In April 2009, a new visitor’s center opened at Monticello, which offers a films and exhibits about the life of our nation’s third president. Monticello also produces many other entertaining educational programs about subjects such as gardening and Jeffersonian architecture, and provides guided tours of the house and grounds. For information about tours and events, and to reserve tickets, visit their website.

Ash Lawn-Highland
Ash Lawn-Highland, the home of James Monroe, fifth president of the United States, is located about four miles from the Inn at Monticello. It is owned and operated by The College of William and Mary, Monroe’s alma mater. Daily tours are available. Ash Lawn-Highland also hosts weddings and other special events. Go to their website for information.

Montpelier was the home of James Madison, fourth president of the United States, and his popular wife Dolley. The house recently underwent a complete restoration and has a monumental archeological effort underway exploring new sites on the outside. It is located in Orange, Virginia, about 27 miles north of the Inn at Monticello. The estate consists of more than 2,600 acres. Just as Jefferson is remembered as the author of the Declaration of Independence, Madison is known as the “Father of the Constitution” of the United States. Some days you can see and speak with Mr. and Mrs. Madison! The house is open for visitors on a daily basis, and the property serves as the site of the Orange County fair and the Montpelier Hunt Races. See their website for details about visiting and events.

Historic Michie Tavern
Michie Tavern, built in 1784, is located about 1.5 miles from the Inn at Monticello. Now a collection of lovingly restored buildings, it is worth the visit if only to see the efforts to sustain older buildings. The Tavern conducts daily tours and serves a wonderful luncheon buffet featuring fried chicken, southern-style vegetables, cornbread, and desserts. Check out its website.

University of Virginia’s “Academical Village” and the Rotunda
The University of Virginia, designed by Thomas Jefferson and built on land owned by James Monroe, was founded in 1819 and opened its doors to students in 1825. Visitors may tour the “academical village” and the Rotunda, and see original letters and drawings from Jefferson in the Special Collections Library. The Rotunda is undergoing restoration in 2014-16, but is open to visits. Also available for viewing is a room that was occupied by Edgar Allen Poe, a student at the University in 1826. Even when the University is not in session, there are many things to do and see. For information about UVA, go to their website.

Pine Knot
In 1905, president Theodore Roosevelt and his wife purchased a rustic cabin and 15 acres in Albemarle County. The Roosevelts stayed in the cabin on eight occasions between 1905 and 1908. In 1941, Mrs. Roosevelt sold the property to a neighbor. Today Pine Knot is owned and maintained by the Edith and Theodore Roosevelt Pine Knot Foundation. It is open to tours by special request. Please go to and for more information.

Woodrow Wilson Presidential Library and Museum
In 1912, Woodrow Wilson became the twenty-eighth president of the United States. President Wilson was born in nearby Staunton, Virginia, and he attended the University of Virginia Law School. His presidential library and museum (exhibiting his beloved Pierce-Arrow automobile) are located next to his boyhood home, and they are open to the public. For more information about tours and other services, check out this website.

Civil War Battlefields
Central Virginia played an important role in the Civil War. Richmond was the capital of the Confederacy; Chancellorsville (1863) and the Wilderness (1864) were significant battles that took place just to the north of Charlottesville, in Spotsylvania and Orange Counties. The Civil War ended at Appomattox Courthouse, about an hour to the south.

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Wineries & Wine Tours

The Inn at Monticello is the perfect home base for exploring Virginia’s wine country. There are more than 30 wineries within 40 minutes of the inn, including Jefferson Vineyards (next to Monticello), Trump Vineyard, and Blenheim Vineyards (owned by the Dave Matthews family), which are just down the road.

As Food & Wine’s own Ray Isle recently observed, Virginia is among a handful of up-and-coming American viticultural regions “producing some remarkable, can-compete-with-anybody wines.” See why Life Magazine in June 2005 named The Inn at Monticello as the place to stay when visiting “the Best New Place to Drink Wine: Charlottesville,” and why Drinks Magazine, Summer 2007, described The Inn at Monticello as “a perfect base for touring, whether your interest is in wine or history.”

In 1773, Thomas Jefferson gave 400 acres near Monticello to establish the first commercial vineyard in Virginia and the American colonies. Now, with more than 260 vineyards across the state, Virginia has become the nation’s fifth largest wine producer, and a destination for the wine enthusiast.

There are seven viticulture areas in Virginia with the Monticello AVA surrounding the inn and 30 member wineries to choose from within an easy drive. For information about Charlottesville area wineries, go to The Monticello Wine Trail and plan your visit. And for a fascinating story involving Thomas Jefferson’s intrigue with wine, read The Billionaire’s Vinegar, by Benjamin Wallace, available at the Monticello Gift Shop or at leading bookstores.

Virginia Wine Tours:
Call us at ­­­­434-979-3593 for more information.  Currently we are not accepting new requests for guided wine tours through our affiliate, Vinnmont, but we can refer you to other wine tour operators that will take you to visit some of the magnificent wineries in our area. 

Recommended Virginia Wine Tours:
If you decide to do a self-guided wine tour, we recommend these wineries and areas around Charlottesville:

Close by and easy to find:
Just between Monticello and Ash Lawn-Highland sits Jefferson Vineyard. Visitors can sample their exceptional wines in the tasting room, and then enjoy a bottle or glass on their outdoor patio.   A short ride past Ash Lawn-Highland is Blenheim Vineyards.  Blenheim is owned and operated by the family of well-known musician Dave Matthews, and has a beautiful recently expanded tasting room and porch.  Completing the “easy and close” wineries tour is First Colony Winery, followed by Wisdom Oak Vineyards (off the beaten path – try their PV), and finally to a spectacular newer vineyard, Pippin Hill Farm & Vineyards.  Pippin Hill offers wine and food tastings on its porch, with magnificent views of the Blue Ridge Mountains.

Great Scenery to the West:
To the west of Charlottesville are some extraordinary vineyards known not only for their great wines, but also for wonderful scenery. King Family Vineyards is set against the Blue Ridge Mountains. Visitors can take in a polo match while sampling their finer creations. Slightly more to the west is Pollak Vineyards. In a short span of seven years, Pollak has become recognized for making some of the best wines in Virginia. Not far from Pollak is Veritas Vineyard and Winery. We love Veritas not only for its great wines, but also for its seductively comfortable tasting room and its special events. Also out west are several other favorite wineries, Cardinal Point Vineyard and Winery, and White Hall Vineyards. Both make some superb wines, especially whites.

History and Rolling Hills to the North and East:
To the east of Charlottesville are some great wineries located on historically significant lands. About 15 miles north of the Inn, on Route 231, is Keswick Vineyards. Keswick is part of an estate that served as a stopping point for British Colonel Banastre Tarleton just before his raid on Charlottesville on June 4, 1781. The property also became an encampment for Confederate soldiers who fought in the 1864 Battle of the Wilderness. Keswick now makes award-winning wines there. Just up the road from Keswick is Barboursville Vineyards. On the grounds at Barboursville are the ruins of a home designed by Thomas Jefferson and owned by his good friend, former Virginia Governor James Barbour. The house was built in 1814, but was destroyed by fire on Christmas day, 1884. In 1976, the Zonin family from Italy bought the property with the idea of establishing a vineyard. Today, Barboursville produces some of Virginia’s finest wines. Barboursville Vineyards is also the site of an award-winning restaurant, the Palladio, which is named after the classical architect who inspired Thomas Jefferson.

Barboursville is not far from Montpelier, the Orange County home of James Madison, fourth president of the United States. There is no winery on the property, but Montpelier is the site of many wine festivals and other special events, particularly the Orange County Fair and the Montpelier Hunt Races, held annually on the first Saturday in November. The house has recently undergone a complete restoration and is well worth a visit.

Close to Barboursville and Keswick Vineyards and Montpelier are three more contemporary wineries, Horton Vineyards, Burnley Vineyards, and Reynard Florence Vineyard.These also offer a diverse selection of excellent wines made from Virginia grapes, especially Norton at Horton (a favorite of UVA ‘Hoos and other fans of Dr. Seuss).

A newer winery to the north and west of Charlottesville is Glass House, located in Free Union.  Part of their tasting room is a greenhouse where the owners, Jeff and Michelle, grow tropical plants.  Enjoy a glass or bottle of their terrific wine surrounded by banana trees that are 15 – 20 feet tall! Further north, visit DuCard and Sharp Rocks Vineyards for pure mountain views and a chance to stop and hike along the way on Old Rag.

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Suggested Day Trips

Located less than a mile from Route I-64’s Exit 121, The Inn at Monticello is a great starting place for exploring Virginia attractions. All excursions will take a half to a full day.

Shenandoah National Park, the Skyline Drive and Luray Caverns
The Skyline Drive runs 105 miles north and south along the crest of the Blue Ridge Mountains in Shenandoah National Park. Enjoy magnificent views looking west towards the Shenandoah Valley, or east towards the Piedmont. Hike the Appalachian Trail; savor a picnic lunch; take in the park’s spectacular fall foliage, or its spring wildflowers. To begin this day trip, enter the park from Exit 99 at Afton, about 22 miles west of the Inn via I-64. Proceed north about 73 miles to Thornton Gap, and exit at Route 211, heading west towards Luray, where you can visit the Luray Caverns. Enjoy the beauty of the Shenandoah Valley heading back to Charlottesville via I-81, or local roads.

The Blue Ridge Parkway, Humpback Rocks, Peaks of Otter, Natural Bridge, Lexington
Like the Skyline Drive, the Blue Ridge Parkway follows along the Blue Ridge Mountains, beginning at Afton Mountain, off of I-64, and proceeding 469 miles south to Great Smoky Mountains National Park in North Carolina. Close to the northern entrance to the Parkway is Humpback Rocks, an outcropping of stone that affords a 300-degree view of the Shenandoah Valley and points to the east and north. To the south, at mile markers 84 to 87, are the Peaks of the Otter, a cluster of 3 mountains close to 4,000 feet in elevation. At one time, Thomas Jefferson thought that these peaks were the tallest in North America. Exiting the Blue Ridge Parkway to the northwest on Route 43, pick up I-81 heading north about 15 miles to Route 75 and Natural Bridge. Thomas Jefferson was so impressed with Natural Bridge that he purchased it in 1774 — from the King of England! Leaving Natural Bridge and heading north on I-81, proceed 12 miles to Lexington, and visit the town and the campuses of the Virginia Military Institute and Washington & Lee University, where Robert E. Lee is buried.

Historic Appomattox Courthouse and Thomas Jefferson’s Poplar Forest
An easy 80-minute drive from the Inn at Monticello is the town of Appomattox Courthouse, where on April 9, 1865, General Robert E. Lee surrendered to General Ulysses S. Grant, ending the Civil War.

Not far from Appomattox is Thomas Jefferson’s private retreat, Poplar Forest. Built in the shape of a perfect octagon, the house is a testament to Jefferson’s fascination with neoclassical architecture. The house has been undergoing an extensive restoration, which is mostly complete. Tour the house in a small group under the direction of one of the experienced guides, and take in the extensive grounds at your leisure.

Colonial Williamsburg, College of William and Mary, Jamestown and Yorktown

About 120 miles to the southeast are Colonial Williamsburg (, the College of William and Mary, Jamestown, and Yorktown. In 2007 Jamestown, the first permanent English settlement in North America, celebrated its 400th anniversary. Williamsburg, dating to 1632, became the leading center of government, education, and culture in Virginia prior to the American Revolution. The historic parts of the city have been restored by the Colonial Williamsburg foundation. The College of William and Mary is the second oldest college or university in the U. S. Thomas Jefferson and James Monroe studied there. Yorktown, of course, is where Lord Cornwallis surrendered to George Washington in 1781, ending the American Revolution. Visiting all of these sites is a full-day undertaking, but it is well worth the trip.

James River Plantations and the City of Richmond
Along the James River, to the east of Richmond, are five beautifully preserved estates – the James River Plantations, all with interesting histories. Sherwood Forest was the home of the tenth president of the U. S., John Tyler. William Byrd II, founder of Richmond, built Westover in 1730. Shirley Plantation, started in 1613, is still owned and occupied by the same Carter family that originally settled there. Evelynton was built by William Byrd II as part of Westover, and was the scene of some major skirmishes during the Civil War. The house was burned during the conflict and re-built in 1937. The most famous plantation, Berkeley, is known as the site of the first official Thanksgiving in 1619; the birthplace of Benjamin Harrison V, a signer of the Declaration of Independence; the birthplace of William Henry Harrison, ninth president of the U. S.; and the ancestral home of Benjamin Harrison, twenty-third president of the U. S. Berkeley and Shirley are available for tours, and are highly recommended.

The City of Richmond, located about 70 miles east from the Inn at Monticello, has many wonderful places to visit. For those fascinated by early American history, one must-see place is St. John’s Episcopal Church, where on March 23, 1775, Patrick Henry uttered these famous words while urging rebellion against the English crown: “I know not what course others may take; but as for me, give me liberty or give me death!” Just about every Sunday at 2:00 p.m., from May to September, an actor portraying Patrick Henry presents his memorable speech.

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Outdoor Adventures

The Inn at Monticello is your base for Virginia adventure travel.  From hot air ballooning, horseback riding, swimming, fishing, and boating, to hiking the Appalachian Trail, there are many outdoor activities for you to enjoy during your stay here in Charlottesville.

Here are some of our favorites:

Charlottesville has some superb exercise facilities. ACAC operates a beautiful new gym with swimming pools, exercise machines, indoor running track and treadmills, free weights, and separate rooms for yoga and aerobic training. It is located in downtown Charlottesville, about a five-minute car ride from the inn. Ask us about obtaining a guest pass.

Running, Walking, Hiking, Biking:
Did you know you could walk from The Inn at Monticello to Monticello? The trail starts at Secluded Farm, right across Route 20 from our property, and continues on the Saunders Trail at Kemper Park to the Monticello Visitor Center, a distance of 2.4 miles each way. There are also many other well-defined trails that start at Secluded Farm and lead to places such as Carter Mountain. The views looking west from Carter Mountain to the Blue Ridge Mountains, and looking east to the horizon are absolutely spectacular, and they make it easy to understand why Thomas Jefferson longed to return to Monticello after his service as president.

The Rivanna Trail is another great place to run, walk, or bike around beautiful Charlottesville. It stretches 19.7 miles throughout Charlottesville, and it is a scenic and well-maintained trail.

For the hiking enthusiast, there are miles of beautiful trails in Shenandoah National Park and the Blue Ridge Mountains. A favorite trail that features lots of waterfalls is the Crabtree Falls trail. Located just off the Blue Ridge Parkway, Crabtree Falls is a succession of cascades dropping almost 1,500 feet over a distance of 3.5 miles. At the end of the Crabtree Falls trail, hikers can connect with the Appalachian Trail.

Charlottesville was recently named one of the top 10 fittest cities in America!

There are numerous competitive and recreational events for runners and joggers in Charlottesville. The Charlottesville Track Club sponsors many races, including the Charlottesville 10-Miler, held in April; the Women’s 4-Miler, held on Labor Day Weekend; and the Men’s 4-Miler, held in December. Ragged Mountain Running Shop is devoted to fitness through running and organizes or participates in many races each year. Look for the Charlottesville Marathon, also held in April.

Fishing, Kayaking, Canoeing, Float Trips
There are some great trout fishing streams that come down out of the Blue Ridge Mountains and the George Washington National Forest. For a magnificent day of fly-fishing for large rainbows, contact our friend and fellow B&B owner, John Roberts, at In Charlottesville, the Albemarle Angler runs trout fly-fishing trips on nearby streams. And in Scottsville, about 17 miles south of The Inn, several outfitters offer bass fishing, kayaking, canoeing, and float trips on the James River.

Horseback Riding:
Charlottesville has some beautiful horse farms that are available for riding. Our friend, Patty Swygert, offers horseback riding and lessons at Mahalo, her farm in Earlysville.  Please call 434-973-3229 for information and reservations.  Fairhunt, near Scottsville, offers trail and rink riding. Call Carriage Hill Farm (434) 296-2672 in Keswick, and Dave or Sally Lamb at Oakland Heights Farm, (540) 832-3350, around Gordonsville, for more information about trail rides and lessons.

Hot Air Ballooning:
Enjoy the beauty of central Virginia and the Blue Ridge Mountains from the air! Take a magical hot air balloon ride with Bear Balloon, Blue Ridge Balloon, or Monticello Country Ballooning.

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Arts & Galleries

Take some time to explore the fine arts in Virginia during your stay at The Inn at Monticello.  Charlottesville attracts both artists and historians with its fine art galleries and museums.

The McGuffey Art Center
An art association and working artist cooperative, located just one block from the downtown mall. The art center contains three galleries, an amazing gift shop, a glassblowing studio and resident artists with open studios.

Kluge Gallery of Australian Aboriginal Art
The Kluge-Ruhe collection of Australian Aboriginal Art is the finest accumulation of artwork of its kind in America.

University of Virginia Fralin Art Museum
The University of Virginia Art Museum maintains a collection of more than 10,000 art objects from all parts of the world.

The Barn Swallow
The Barn Swallow features a diverse collection from over thirty artists. The gallery exhibits and sells pottery, jewelry, glass, textiles, and one-of-a-kind pieces.

Second Street Gallery
The Second Street Gallery exhibits contemporary works in rotating exhibitions. It is located in the same building as the Live Arts Theater.

Graves International Art Since 1978, Graves International Art sells only original art, hand-made prints and paintings by the world’s leading artists. No signed reproductions, only original works of art from the 1500’s to the present, and from Raphael to Roy Lichtenstein.

UVA Special Collections Library
The UVA Special Collections Library collects old documents, manuscripts, books, and literary works, and sponsors exhibits. Among the documents in its collection are thousands of original letters and papers from Thomas Jefferson, and original letters and documents about the Declaration of Independence.

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