Charlottesville, VA - Jim Flynn's BestWeekends

Charlottesville, VA

Charlottesville, VA Overview

Nestled in the shadows of the Blue Ridge Mountains, Charlottesville, Virginia is a largely undiscovered destination for weekend travel, yet offers everything you would want for an enjoyable getaway; great accommodations and dining and plenty of interesting things to do. Charlottesville is best known as the home of the University of Virginia and Thomas Jefferson’s beloved Monticello  and while a visit to Monticello is worth the trip alone, Charlottesville is so much more than just that.

Two other presidents, Madison and Monroe had homes here that are major tourist attractions and this city of 45,000 residents has a vibrant music scene, wonderful art galleries, ACC college sports, nationally recognized wineries, terrific shops and cafes in a Downtown Pedestrian Mall, great golf courses and a host of other indoor and outdoor recreational activities.

Known affectionately by the locals as C-Ville, Charlottesville is one of those places you visit where you think, “I could live here”. Physically it is a small town with small town manners, but it’s got big city lodging, dining and activities, making it a perfect weekend getaway.

When To Go

There is so much to do in and around Charlottesville that you can enjoy the city at any time of year. The warmer months provide the opportunity to enjoy the vast array of outdoor sports and sidewalk cafes. Fall in the Blue Ridge Mountains is spectacular and winter means ACC basketball.

Getting There

Richmond, Va is the closest major airport, a little over an hour away. Driving time from DC is about 2 hours, 20 minutes, Charlotte and Philadelphia about 4 hours 45 minutes and New York about 6 hours. We drove from central New Jersey, it took about 5 1/2 hours and was a very pleasant ride through the country.

Getting Around

You will need a car when traveling to Charlottesville, particularly if you want to explore the wineries and historical venues. If however, those hold no appeal and you are staying at Keswick Hall with all it has to offer, you could get by without a car.

Things To Do

The question is really what would you like to do, not what is there to do. Outdoors there’s fishing, biking, hiking, horseback riding, canoeing/kayaking and golf. Indoors there’s history, art galleries, antiquing, museums, theater, music and college sports. An exciting wine community offers tasting opportunities and there’s no shortage of wonderful places to shop.


If you are fortunate to be staying at Keswick Hall, you’ll be given a temporary membership to their private club which is a wonderful golf course. Birdwood Golf Course at the Boar’s Head Inn is the next best thing and the favorite of many locals. Birdwood is currently undergoing extensive renovations overseen by Davis Love III.


Keswick Hall, the Clifton Inn and the Boar’s Head Resort, three of our Featured Properties have tennis facilities. Charlottesville, Albemarle and Monticello high schools and UVA have lit courts and the Wintergreen Resort just west of the City has 19 clay courts and 3 indoor courts. Non-guests pay a fee.


Three great places to take advantage of the beautiful countryside; Shenandoah National Park, Rivanna Trails, Sugar Hollow with its 48-acre reservoir and Sanders Monticello Trail.
Boar’s Head has a wonderful trail system over its nearly 600 acres.


Keswick Hall has three pools, a spectacular Infinity pool overlooking the sprawling golf course below, a pool at the spa and a pool at the Tennis Center. Both have drink and snack service. The Clifton Inn also has an Infinity pool with a waterfall set back in the forest, walking distance from the Inn. Boar’s Head Inn has an outdoor pool and  ACAC, the downtown fitness center has an indoor pool.


ACAC, downtown at 111 Monticello Ave, is a fully appointed fitness center with racquetball and squash courts and an indoor aquatics center. Keswick Hall and Boar’s Head have fitness centers.


You can fish on your own in Shenandoah National Park or for someone who really knows the local fishing holes, contact the Albemarle Angler for guided tours. Half and full day trips from $195.


James River Runners has been outfitting boating enthusiasts for over 30 years. Canoe, kayaking, rafting and tubing trips are available on the James River.

Horseback Riding

There may be no better way to experience and appreciate the beauty of the area than on horseback the way Thomas Jefferson and James Madison did so many years ago. Oakland Heights Farm offers rides any skill level and will even take you on the actual trails our former presidents used. $40pp

Day Spa

Oasis Day Spa and Body Shop, W. Water Street. Voted the “best” by the locals, they do it all and at very reasonable prices. Most massages are under $100 which is almost unheard of these days. Keswick and Boar’s Head have their own spas.


No visit is complete without a stop at Jefferson’s beloved Monticello and it is worth the trip to experience the genius of this man. Two other presidents, James Madison and James Monroe, also made their homes here and are popular tourist stops. Madison’s Montpelier and Monroe’s Ash-Lawn Highland are wonderful examples of that period’s architecture and property. Historic Michie Tavern was the social center of the community in Jefferson’s day and visitors can tour the original tavern and participate in an interactive tour.


In town everyone’s favorite is Circa at 17 Allied St. They’re goal is to fill the void between junk stores and pricey antique “shoppes.” and they do a pretty good job at it. Pick up a copy of Sunday Driver Directories for a complete list of antique stores on Rt. 29 North and the surrounding area.


The (UVA) Virginia Cavaliers play in the exciting ACC and field 12 men’s and 13 women’s sports.

Vineyard Tours & Tastings

There are 24 wineries in the immediate Charlottesville area.  The Monticello Wine Trail Guide and Map is available around town in a brochure. The Virginia Winery Guide for the entire state is available also in a brochure. Three vineyards not to miss; King Family Vineyards (they have polo matches here), Barboursville (excellent restaurant, Palladio) and Trump (beautiful setting and good wines).


Charlottesville has a dynamic art community with galleries and museums for the art lover to enjoy. McGuffrey Arts Center, located one block from the Downtown Mall, is one of the oldest artist-run cooperative art centers in the country


Every Friday from early May to early September, national and local acts in many genres are staged at the Sprint Pavilion for free outdoor entertainment. The historic Paramount Theatre opened in 1931 and today presents just about any kind of music you can image from classical, pop, jazz, opera, folk and more. Movies too. Very cool Greek Revival-influenced façade. Interior evokes thoughts of Radio City Music Hall.  UVA’s John Paul Jones Arena is a 15,000 seat venue that is the home of the school’s basketball teams and hosts popular artists like Neil Diamond, Eric Clapton and others. The Charlottesville Symphony at UVA is a unique blend of professional musicians – many of whom are also music faculty members at the University of Virginia – accomplished community members and talented university students from diverse academic fields. Fridays After Five continues to be Charlottesville’s favorite live concert series. of free live music and fun. April-September.


Barracks Road Shopping Center on Rt 29, has the national chains like Old Navy, Barnes & Noble, Bed, Bath & Beyond, Ann Taylor and others of that kind, but it is the local stores that hold the most appeal like; The Happy Cook, The Virginia Shop, Oil & Vinegar, Shenanigans, Scarpa, Quilts Unlimited to name a few. Downtown Mall has lots of interesting boutiques like The Jeweler’s Eye, Clock Shop, Yves Delorme, novel, Caspari and more.


The Virginia Festival of the Book, attracts big names in literature for five days of signings and readings.  Charlottesville Opera, is one of the world’s leading opera festivals, held mostly at the Paramount Theater. The Know Good Beer Festival features local beers and beers from around the country. held in January. Lockin’ 4 day music festival drawing 30,000 people and 50 acts. June.

Dont Miss

  • Jefferson’s Monticello
  • Stroll the UVA campus and take the Rotunda tour
  • The Downtown Mall
  • Lunch at Palladio at Balboursville Vineyards
  • Dinner on the Terrace at Fossett’s
  • A visit to Trump  Winery and Vineyard
  • City Market, Saturdays, April-October

The Best Of...

News and Resources

The Daily Progress is the local newspaper and C-Ville is a weekly with news and arts info.

Food & Drink

Early Morning Coffee

Of course, all our Featured Properties offer coffee for their early risers, but if you are out and about and need a fix head to Mudhouse at the Mall. Opens at 6:30am. When Mudhoue gets to crowded, locals flock to Shenandoah Joe’s. These folks are serious about their coffee! Always voted best coffee in town.


Again our recommended lodgings all offer a delicious breakfast, but the locals are passionate about Bluegrass Grill and Bakery (Think biscuits and gravy.) on Second Street and Bodo’s on Preston. Killer bagels. Marie Brette brings a touch of France to C-Ville, serving breakfast, brunch and lunch. Amazing croissants and the baked eggs, country ham hash and stuffed French Toast are to die for.


You won’t want to miss one lunch at Palladio’s at the Barboursville Vineyard. Excellent wines and delicious Italian fare.  Revolutionary Soup, 2nd Street SW has, go figure, amazing soups and pretty good salads and wraps as well, Petit Pois from the owners of Fleurie is a charming French bistro on the Mall, Citizen Burger Bar for a decadent burger, also on the mall, Hamilton’s on the Mall has excellent food and people watching, Trump Winery has delicious sandwiches, salads and cheese platters while you taste their wines and Fossett’s offers great food and a wonderful terrace overlooking the golf course. The Mill Room Terrance, overlooking a lake at the Boar’s Head Resort is a delightful lunch setting. You can also grab some food at Feast in the Main Street Market and find a table not associated with a restaurant on the Mall have have your own people watching picnic.


Citizen Burger Bar’s Citizen Burger; local grass-fed beef, McClure cheese, blackened onions, garlic aioli, iceberg, and tomato on a brioche bun and a fried pickle spear.

Raw Bar

Public Fish & Oyster features fresh East Coast Seafood, Raw Bar, craft beers, cocktails and a comprehensive wine list.

Wine Bar

Tastings is a wine bar, restaurant and wine shop. Orzo Kitchen & Wine Bar. This is a cool place for lunch, a drink or dinner, but absolutely perfect for a late afternoon snack and a glass of wine. They call it Siesta time and offer a bunch of small plates and $5 glasses of wine. Perfect….Cheese, wine, snacks? Head to Tilman’s Cheese and Wine. C&O has won tWine Spectator Award of Excellence every year since 1996

Ice Cream

Chaps on the Mall. Gourmet ice cream for 15 years. All natural ingredients, nothing artificial. Open late on nice nights.


Downstairs at C and O is a great place for a drink anytime. Bang has tapas, great drinks and a terrific outdoor rear patio and Hamilton’s makes a mean martini. Alley Light (oddly down an alley, under a light) has fantastic drinks (fresh squeezed juices and homemade tonic) and small plates. A true craft cocktail bar and not to be missed. If you are a beer person, you’ll want to make a stop at Three Notch’d Brewing Company.

Activities & Shopping

After Dinner Fun

If you’re drinking for after dinner fun head back to Siips for some wine. Dave Matthews got his start at Miller’s, originally an old-time apothecary and its still the spot for jazz and local folk in a dark and sexy space. Wanna dance? Rapture’s R2 is the nightclub and dance floor on the Mall. Easy listening? Jazz at Hamilton’s on Saturday nights.

Picnic Fixins

Baggby’s Gourmet Sandwiches and Take It Away make great sandwiches, but my favorite is Feast at the Main Street Market. Wonderful sandwiches, amazing charcuterie selections.

Wine Store

Locals rave about the Market Street Wineshop, but I really liked Tastings. They have a wine bar and also serve food. Great selection.

Take It Home

Albermarle Baking Company, Main Street Market has wonderful Artisan breads, but get there early because they often sell out. Delicious specialty desserts, too. Gearhart Chocolates, also at the Main Street Market. Made with premium chocolate, local sweet cream and pure butter and then they add fresh fruits and nuts. You won’t be able to resist these amazing chocolates.

Special Things

Up, Up and Away

Take a spectacular hot air balloon ride over the Virginia countryside with Bonaire Charter or Blue Ridge Balloon Co.and finish with a champagne toast, all $210pp

Lunch Among The Vines

Enjoy a spectacular lunch at the Palladio Restaurant at the Barboursville Vineyard…..and make sure you pair it with their delicious wines.

Where To Stay

Boar’s Head Resort

OVERVIEW of Boar's Head Resort

The history of the Boar's Head Resort property dates back some 300 years and has ties to Thomas Jefferson. The 3,000-acre tract that the resort resides on was part of Virginia's first land grant in 1734, and Terrell's Ordinary, an inn for westward travelers, opened at the exact location…

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Keswick Hall

OVERVIEW of Keswick Hall

There is much to enjoy in Charlottesville, but it will be a struggle to leave the confines of the exquisite Keswick Hall, located just outside of town in the rolling hills of Virginia hunt country. In fact, with its beautiful rooms, wonderful dining, great golf course and spa and excellent…

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Oakhurst Inn

OVERVIEW of The Oakhurst Inn

Considered Charlottesville’s first contemporary boutique hotel, Oakhurst Inn is composed of four Craftsman-era residences that date back to 1913. These buildings served as student and faculty housing until 2012 when the thoughtful 18-month renovation began. The renovations focused on preserving the unique architectural features of the residences while also incorporating…

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The Clifton

OVERVIEW at The Clifton

You feel you are in for something special as you pass through the property gates of The Clifton and ascend the stone driveway to the stately Southern mansion perched at the top of the hill....and you won't be disappointed at this stunning Relais & Chateau property. The…

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Where To Eat

1799 at the Clifton Inn

You would not have experienced the best Charlottesville has to offer if you missed dinner at the Clifton Inn during your stay. Housed in a magnificent 18th century building on 100 acres of wooded beauty, the restaurant sits perched above a private lake in a setting sure to set hearts aflutter. The evening should begin…

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Almost every time we travel, we are introduced to something new on a tip from a local. Such was the case during our last trip to Charlottesville when someone recommended Bizou. Housed in a former dive bar on the Downtown Mall, this eclectic restaurant was the "find" of our last trip. Much from the old…

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C & O Restaurant

Driving by you'll almost miss this brick former railroad flop house on East Water Street until you see the C&O Pepsi Cola sign out front. You begin to wonder if this is the right place until you step inside the dark and intimate mezzanine area with its brick walls, hardwood floors and beamed ceilings. With…

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Hamilton’s at First & Main

Hamiltons, located on the Mall is the perfect place for lunch or dinner especially in the warm months when you can sit outside on the patio and people watch. Inside it's bright and cheerful, decorated in yellows, blues and pinks with hardwood floors, an oak bar, exposed duct work and funky artwork. Floral fabric booths…

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Marigold Restaurant by Jean George

The cuisine at Marigold by Jean-Georges reflects a passionate commitment to fresh, local and organic ingredients. The menu changes often to offer sustainable and seasonal produce that is at its peak – much of it grown at their own nearby farm. Meat, fish and dairy are locally sourced, where possible, from humanely treated, pasture-fed animals…

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Mas Tapas

Sometimes when I am on the road, I need a break from the upscale restaurants we go to every night and just want to kick back, drink some wine, have a casual meal....and a bill that doesn't break the bank. Mas Tapas is just that kind of the neighborhood restaurant we all wish we had.…

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The Mill Room at Boar’s Head Resort

The Mill Room is the signature restaurant at The Boar's Head Resort, but its wonderful lakeside setting and creative menu make it a worthy stop even if you are not staying at the resort. This AAA Four Diamond restaurant offers cozy inside dining with hardwood floors, beamed ceilings and intimate booths. Outside the terrace overlooks…

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