Charlottesville, VA, while always known for being a quaint and lively college town, is on the map thanks to accolades including “Top 10 Hippest Mid-Sized Cities”, “8 Southern Cities for your Bucket List”, “Top 100 Best Places to Live”, “12 Cutest Small Towns in America”, and the list goes on and on.

I’ve had the pleasure of living in Charlottesville for one year as I completed my masters, and I have continued to return for three weeks each summer to facilitate a program for visiting international students. To top it off, I am thrilled to call Charlottesville my next home, as I just accepted a full-time position at UVA as an Education Abroad Advisor! (This is a big and exciting deal as my work has previously involved a majority of contracted roles and “home” has been where my suitcase is. Hurray for furniture shopping, homemaking, and my dream job!!!)

From stunning hikes, amazing food, orchards, wineries, college sports, an incredible music scene, and even an airport, Charlottesville has it all. Read the following as you begin to plan your visit!

Take a Hike

Whether you have 2 hours to spend at sunset after a long day of work or wine tasting, or want to tackle a stout 20 mile day, there is something for you in the Shenandoah. My favorites include Blackrock Summit – short and sweet, Humpback Rock – less short, a little grueling, but perhaps even sweeter, Three Ridges – a challenging and stunning loop in Nelson County, stunning views await you!

My favorite hiking guide is Hiking Upward. With accurate trail info, reviews, and plenty of photos – it’s in excellent tool in adequately planning your jaunt! For a list of favorites, check out Pink Caddy Travelogue’s recommendations.

Enjoy Live Music

As a big bluegrass fan, Charlottesville never disappoints. Check out the venues The Jefferson, The Southern Cafe and Music Hall, and my true favorite, The Garage.

In the summertime, plenty of venues offer free, outdoor live music. A long-time favorite is Fridays After Five held at the Pavillion on the downtown mall. This year will be their 32nd year of free music. From April to September, this is the place to be!

When in Charlottesville, Thursdays are my personal favorite because of the Carter Mountain Sunset Series. From May – September, bring your pals and your picnic blanket and get ready to fast your eyes upon a beautiful sunset while filling your bellies with apple cider donuts, wine slushies, bbq sandwiches, and more. Come Thursday, (and now also on Wednesdays due to COVID and limited space) this place is the place to be!

If you’re lucky, you’ll get to catch an artist at The Garage. This small, intimate venue is exactly as it sounds. After a weekday trivia night, my friends and I decided to check it out on a whim and it has become one of my favorite things about Charlottesville! Pack your picnic blanket and bring your tribe (pups welcome), and enjoy an intimate music experience with amazing acoustics.

EAT!

Charlottesville has an amazing selection of restaurants. If you are able to do so, plan your trip around Charlottesville’s Restaurant Week! For one week twice a year, restaurants offer a 3 course mix-and-match menu for a fixed price of $26 or $36. CAN YOU SAY YUM?! Restaurant week is coming around again soon – January 24 – January 31! You better believe I’ll be there!

If you have limited meals to spend in Charlottesville, don’t miss Bluegrass Grill and Bakery for breakfast (cash only!), Ivy Provisions for a quick and delicious sandwich for lunch, and Maya or Tavola for dinner (close, close call!).

During my time in Charlottesville, I made a point to document my eating experiences. As there are so many great places to try, I wanted to remember the best of the best. (I hope that this spreadsheet says more about Charlottesville restaurants than it does my tendencies!)

Charlottesville City Market

I’m not a big shopper, but regardless of whether I need something or not, I LOVE perusing the Saturday City Market. From handmade soaps, jewelry, made to order food, fresh produce, and of course, coffee (always my first stop), this is one of my favorite aspects of this town. Speaking of someone who you will see at the City Market, the last thing on my list is…

Take a Goat Cheese Tour and Play With Some Goats at Clover Top Creamery

If you love cheese, learning about local products, and spending time with the cutest goats, make a visit to Clover Top Creamery! While I love all of the aforementioned things, I’ve been on a mission to milk a goat and I did just that this July! This summer, I joined Clover Top for a farm tour and it was my favorite thing I did with my three weeks in town. The owners are amazing – kind and incredibly knowledgeable. They taught us about the goats, introduced us to the different species, allowed me to fulfill my dream of milking a goat (Fiona is the best!), and let us sample their delicious cheese. For $10 a person, you don’t want to miss out! Look for them at the Saturday morning market, too!

Other personal favorites include

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• centering yourself with a yoga class at NOW yoga (the instructors are amazing)
• taking a nature walk on the Rivanna Trail – Riverview Park is my favorite access point
• trying one of the numerous vineyards and breweries – check out the Monticello Wine Trail for a list of upcoming events

Charlottesville’s close proximity to the mountains and to the beach is yet another reason it’s a fabulous town. Furthermore, both Roanoke and Richmond are just over an hour’s drive away.  When you’re ready to explore more neighboring gems, be sure to explore this list of Richmond Day Trips!

I hope you enjoy Charlottesville as much as I do!