Charlottesville Insider's Guide to Wineries, Hotels, Events, Shops, and Restaurants

Charlottesville has wonderfully unique things to do.

Not every town has unparalleled vistas, a Cab Franc made at the hands of the same person pouring it, or Dave Matthews and John Grisham walking by as you enjoy lunch at a café on its historic pedestrian mall—but Charlottesville does.

It’s urban and bucolic, historic yet modern. There are boundless hiking trails, wedding venues, wineries, breweries, boutique retail shops, and theaters (not to mention more restaurant seats than there are people to fill them). It’s for the limitless adventurer, the wine-taster, the music-seeker, and the family searching for a new experience..

At Charlottesville Insider, our goal is simple: to showcase Charlottesville by curating our ideas about what makes it unique. Follow our insiders to see what’s new, find exclusive deals, or simply figure out how to spend your day in our favorite city.

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12 Truly Unique Things to do Around Charlottesville

Show your love with a romantic date night in Charlottesville.

Charlottesville Insider

Carter Mountain Orchard is a Charlottesville favorite, just minutes from downtown Charlottesville and offering stunning views of the city.  Enjoy the festivities of the season - fruit picking, pumpkins, hayrides, live music, and family fun events as well as food and drink - apple cider, baked goods, Carter Mountain Wine, Bold Rock Cider on tap, and last but not least..their famous apple cider donuts! 

Within reach of charming downtown Crozet, pick your own fruit and pumpkins surrounded by beautiful views of the Blue Ridge Mountains. Make a day of roaming through the seasonal fruit and veggie picking then head on over to the Farmers Market for sweet treats and wine! Check out their festive calendar of events!

 in America located about 25 miles northeast of Charlottesville, in Somerset VA!  Don’t miss out on seeing this masterpiece in nature, and marvel at the time and effort put into its creation.  And, pick your own pumpkin and check out their farm market while you’re at it! 

 located just north of Charlottesville in Ruckersville, VA.  Shop for pumpkins, fall plants, and decorations, and enjoy fun family events and festivities like pumpkin painting and their Fall Makers Festival featuring live music, food, and local artisans, and make your own flower bouquets! 

Blue Ridge Mountain Maze at Blue Toad Hard Cider

Experience fall festivities for the entire family!  Located in Roseland, VA at Blue Toad Hard Cider, they offer an array of fun activities including a 5-acre corn maze, giant slides, apple slingshot, farm animals and pony rides, pumpkins, hot cider, kettle corn, apple cider donuts, fresh squeezed lemonade, country store and a whole lot more.  And the best part, mom and dad can sip on a cider and relax after the kids have had their fun! 

This is a “must go” if you’ve never been!

Located in beautiful Afton VA, bring the whole family and enjoy a few hours in the Blue Ridge!  Pick out a pumpkin and have some pumpkin ice cream and cider, then head across the street to Blue Ridge Brewery for dinner and beer! 

Pick your pumpkins, apples, and blackberries!

Six Fall Picks - Pumpkins Galore!

Prost!! BMB really does it up each year for Oktoberfest. German menu specials every day, festive costumes, live music, and more. Don’t miss the Keg Bowling!

Oktoberfest Charlottesville 2023 | What to do for Octoberfest in Charlottesville Virginia

FRIDAY 9/29 | FULL NELSON FRIDAY – $4 FULL NELSONS 5:00-9:00 | LIVE MUSIC WITH BAREFOOT & SUNSHINE 5:30-8:00

SATURDAY 9/30 | LIVE OOMPAH MUSIC 1:00-4:00

SUNDAY 10/1 | LIVE OOMPAH MUSIC 1:00-4:00

TUESDAY 10/3 | KEG BOWLING COMPETITION 5:30-7:00

THURSDAY 10/5 | STEAL THE STEIN ALL DAY! | LIVE ACCORDION MUSIC WITH MILES HOYLE 5:00-8:00

FRIDAY 10/6 | FULL NELSON FRIDAY – $4 FULL NELSONS 5:00-9:00 | LIVE MUSIC WITH CIRCUS MUTT 5:30-8:00

SATURDAY 10/7 | LIVE OOMPAH MUSIC 1:00-4:00 | HILL CITY CLOGGERS PERFORMANCE 5:30-6:00

SUNDAY 10/8 | LIVE OOMPAH MUSIC 1:00-4:00

Visit Whiskey Jar downtown now through October for Oktoberfest festivities and German food and beer!

Pretzels with cheese, Brats, Schnitzels, Steins

Oct 7th, 3-5pm The Original Elbe Musikanten German Band

Charlottesville’s newest brewery presents “Hogtoberfest” this Friday 9/22!

Authentic German food, German trivia, games, Sing and Stein-Hoist-along songs and more!

Dust off your lederhosen and Dirndls for Decipher’s festivities Saturday 10/23!

Prost! to another year of Oktoberfest celebrations at Three Notch’d Charlottesville! 

Limited edition 3NB steins w/ drink specials

Delicious additions to their lunch and dinner menus - Oktoberfest Nachos, Bratwurst Sandwiches, a GIANT pretzel, Pork Schnitzel Platter, & Black Forest Cake

$15 = filled stein (you keep the glass!) $10 = just the stein

10 YEAR ANNIVERSARY 'Hansel & Kettle' Imperial Oktoberfest Lager has been released - on draft and w/ 4-packs available for purchase

Rockfish started the season with new food and drink for Oktoberfest!

Märzen served in German steins, bratwurst cooked in their Märzen with sauerkraut, soft pretzels and spicy mustard

Random Row Brewing is offering a delicious addition to their Billy Pie Pizza menu for Oktoberfest!

The Oktoberfest: A white base pizza with Dijon mustard-rubbed Schweinebraten pork and onions, braised for 10 hours and ending in a delectably spicy fall-tasting pie!

Oktoberfest menu featuring a MASSIVE soft pretzel, Flammkuchen flatbread, an Oktoberfest beer, and a pumpkin beer

Chef Tasting Series; “Harvest” wine pairing October 11th, cider/wine pairing on November 15th

Bratwurst and German potato salad style fries at their food truck

Saturday Sept 30th: Ein Prosit Party 3-9pm (Willie Hayes and the Alpen Travelers, Stein Hoisting, Special menu with Beer Braised Brats, Sauerkraut, Pretzels with Beer Cheese, German Butter Cake, and German Roast Beef Sandwiches, German Beer tap takeover)

Sunday Oct 1st: Brunch and Brew menu with Beer Braised Brats, Sauerkraut, Strammer Max Egg Sandwiches, Pretzels with Beer Cheese, and German Butter Cake, German Beer tap takeover

Oktoberfest Charlottesville 2023

Best Charlottesville Mexican Restaurants

Charlottesville has some great Mexican restaurants to choose from. From Bebedero downtown to the multiple Guadalajara locations, Charlottesville can fulfill your need for margaritas and enchilladas.

Best Charlottesville Mexican Restaurants

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