Dreaming of Travel: Shenandoah National Park and Charlottesville, Virginia

Published on June 11, 2020 - Updated on October 19, 2020

Visit this wonderful family friendly town any time of the year!


“My parents lived in Charlottesville in their mid-20s to early 30s and I also enjoyed a wonderful opportunity to live there while attending UVA. Charlottesville has always had a special place in our hearts and Shenandoah certainly plays a big role in it all.” - Caitlin Iseler, happyly Founder and CEO

Stunning Charlottesville, Virginia is best known as home to the University of Virginia and President Thomas Jefferson, but is also a fantastic family getaway destination. Don’t be surprised at its tug on your heart - many folks plan a visit and end up putting down roots.

With a wholesome yet hip small-town vibe and big town amenities, Charlottesville has a robust college sports scene (shout out to the Cavaliers men's lacrosse and baseball teams and women’s rowing and lacrosse). They are host to everything from concerts and performances from international superstars like Keith Urban and Alabama to Monster Trucks and the Harlem Globetrotters - the variety will make just about any fan a superfan. And did we mention that Dave Matthews Band got its start in C’ville?

For a well rounded weekend, enjoy breakfast at Bodo's Bagels, take a tour of the University of Virginia's beautiful rotunda and lawn, explore King Family Vineyards, and head to the downtown mall for pizza at Christian's or Wayside Chicken for the best fried chicken ever. Escape to the mountains and find yourself lost in the wonders of Shenandoah National Park, wander the historic grounds of Monticello, or bask in the Blue Ridge foothills in Crozet. There’s so much waiting for you in C’ville. Here’s how you can explore it like a local.

The Best Time to Visit


If you’re planning on visiting Charlottesville, your timing can help play a role in your experience. For the most part, May to July is generally the recommended time frame for visiting if you want to avoid the crowds that the local college draws and take advantage of the wine tasting season. It’s right before the summer heat takes over, and the perfect time to wander the mountains and valleys nearby.

The fall, though stunning with changing leaves, will certainly be more crowded in the parks with students, parents and tourists exploring. If the leaves are worth it, you’ll surely be satisfied, but for the most subdued experience, consider opting for the winter instead. It’s quieter for a reason during this chilly offseason, but you’ll have the beautiful sights nearly to yourself, and prices reflect the lack of tourism, giving you a reprieve from the usually more expensive rates.

Experiencing Charlottesville


Dining and Sweet Treats in C’Ville

Bodo's Bagels Family Breakfast

Any local Charlottesville resident will tell you the name of their favorite casual place to dine: Bodo’s Bagels. Dine-in or take out for a family of four for under ten bucks. A little more will get you the #fancystuff like smoked salmon or gourmet cream cheese. Try their egg, bacon, and cheddar on an everything bagel. For lunch, try their heavenly, garlicky caesar salads or daily house-made soups - delish!

Christian’s Pizza

Christian’s Pizza is a local family-owned pizza place with gourmet pies available by the slice. With three locations, it's always a convenient spot to pop in for a quick bite. Kids love good old cheese or pepperoni but mom and dad may want to try roasted vegetable or pesto ricotta or the heartier meatball parmesan. One location is on the downtown mall, which is a pedestrian mall, super safe for walking and strollers. There are specialty stores, outdoor dining options, dessert spots, and gourmet coffee shops.

El Puerto

A clean, delicious and reasonably priced Mexican restaurant that serves something for everyone, this is a great place to bring the entire family. Located at 2045 Barracks Road, it’s only about a mile from the downtown mall.

The Pie Chest

The downtown mall area near the grounds at UVA has wonderful dining choices with a nod toward gourmet, even with the all-American pie. This sweet little gem is tucked in a side alley right off of the downtown mall and is the perfect place to get take out, whether you satiate your sweet tooth or beat the hungries with a savory Chicken Pot Pie selection.

You can also bring the fam, sit inside and people watch while you sample by the slice selections. It’s tough to pick our favorites but we’ll go with S’Mores, apple, and chocolate cream. We love that the pastry chef is inspired by locally grown and seasonal ingredients, such as in the epic summertime strawberry rhubarb pie.

Splendora’s Gelato

Steps from the Children’s Museum, and also on East Main Street (317) this sweet spot delivers a memorable experience for all!

Downtown With Kids

“As a big fan of Charlottesville, having lived there in my youth, it is one of my favored vacation spots. For many years we used Charlottesville as the base for our vacation adventures with the grandkids. On one of those days when the great outdoors is not an option, or you need a few hours to chill indoors, the Virginia Discovery Center is a great alternative.” -Darlene Banks, Ambassador and Grandmother

McGuffey Park

Behind the McGuffey Art Center, near the Downtown Mall in Charlottesville VA sits McGuffey Park. In McGuffey Park much of the equipment is unique, a "weeping water well" water feature, spicas, spinner bowls, and swings. There is a circular bike path as well as a sunken basketball court. In the summer little ones enjoy playing there before a free Friday concert on the mall. No matter the season, though, McGuffey Park is an enjoyable place to spend a few hours.

Jefferson Theatre and the Pedestrian Downtown Mall

Renovated and renowned Jefferson Theatre is a gem in the middle of the beautiful bricked pedestrian Downtown Mall. The Jefferson Theatre is rooted in Charlottesville history, established in 1912. Over the years it hosted silent movies, Harry Houdini, The Three Stooges - the list of historic performances is a long one.

It reopened in 2009 after a full restoration and currently hosts a variety of events, including some geared towards families. Visiting the pedestrian downtown mall is perfect for the family: kids can run ahead a bit, strollers are easy to maneuver and grandma or mom and dad can grab a coffee or glass of wine while the little ones sample ice cream. There is truly something for everyone.

Children’s Discovery Museum

Located at the end of the downtown mall near the music venue Sprint Pavilion, (which seats 3500 - picnicking permitted), The Children’s Discovery Museum has been intriguing the curious since 1981, and now serves the children of the original generation of guests.

Child-focused, community-based, and the only children’s museum in Charlottesville, the mission and goals are crystal clear, to foster a lifelong love of learning and encourage intellectual curiosity by intersecting learning and play. The exhibits change regularly and the museum maintains a strong commitment to both tourism and outreach. A perfect rainy day activity!

Family Fun at the University of Virginia


The University of Virginia (UVA)

The sprawling 1682 acres of grounds at the University of Virginia are perfect for horticulturists, architects, and history buffs but for kids, trick or treating on the Lawn at Halloween is a highlight. Arrive by 3 pm to beat the crowd and get ready for amazing Instagram shots to share with the world! The Rotunda and Lawn don’t need filters. Then tour the area with the kids and say hello to UVA’s student leaders, honored to live on the lawn in historic rooms - they'll be passing out treats and giving your kiddos a glimpse of history.

The Grounds at UVA

A couple of hours visiting the grounds (we don’t say campus here!) will give your family a good look at the spectacular architecture and history. Definite stops: Rotunda, the Lawn, and the Range (this is the backside room on the lawn reserved for graduate students). Must-Sees: Edgar Allan Poe’s room, Scott Stadium, John Paul Jones Arena, and the University Chapel which hosts gorgeous weddings.

Picnic on the famous UVA Lawn

Grab sandwiches to go from Take It Away on the university's beloved 'Corner' (don't forget to ask for their famous house dressing on the side!). Then venture over to the UVA lawn for a family picnic. Let your children run free and enjoy the generally beautiful weather! Kite flying in the spring is super fun, as is hanging around the wedding chapel and spying a bride or two. The chapel books up a year in advance and with good reason - it’s gothic storybook style is stunning.

Picking Fruit at Local Orchards


What’s more wholesome than piling the family in the car and heading to the countryside to pick fruit. Our abundant countryside lends itself to hours of orchard time. Be sure to plan ahead if you plan to do the picking yourself. Fruit production and picking dates are fickle since rain, frost, and sunshine make a difference in the growing seasons as well as the yield.

Carter Mountain Orchard

We recommend Carters Mountain Apple Orchard near Monticello. In the fall Carter’s Mountain hosts wagon rides and apple activities as well as delicious gourmet apple cider and apple donuts. The picking is plentiful and the scenery is spectacular.

Chiles Orchard

Located in Crozet for peaches, apples, and strawberries. Both are great with families. Chiles is also very kid-friendly and hosts families and school groups from May until October covering strawberry, peach, and apple seasons.

Head For The Hills

Crozet, Virginia

Crozet, a cute little village 20 minutes west of Charlottesville bustling with new housing options, vineyards and breweries and gourmet food. Crozet is a must visit sweet spot near the best local orchards, wineries and outdoor activities. Crozet has wonderful restaurants, hikes, and peach picking.

Misty Mountain Camp Resort

Misty Mountain Campground, RV Park, and Cabins offers kids games and activities and a pool area. They also offer day passes!

Misty Mountain has long been part of incredible family memories, starting with cabin rentals almost 15 years ago, to most recently visiting with a camper. The property has grown and the owners have invested in wonderful upgrades. Family-friendly features include a game room, a new playground, music and party areas, and a pool and splash area too. The general store is well equipped and priced reasonably too.

Crozet Pizza

“Tossin’ Dough” since 1977, this family owned pizza place is known for some of the best pies in the area, and according to National Geographic, the world. It’s open everyday but Tuesday and often hosts live music and games at 5794 Three Notched Road in Crozet, which is about twenty minutes from campus.

Chiles Peach Orchard

Pick your own fruit at this orchard right in Crozet, Virginia.

Greenwood Gourmet Grocery

Located at 6701 Rockfish Gap Turnpike in Crozet, this place is a gem. You can stock up on wine and specialty groceries, really everything you’ll need for a Misty Mountain stay.

The Inn at Sugar Hollow Farm

This gorgeous bed and breakfast (currently functioning as an entire house rental at $800 per night due to COVID-19) boasts 5 available bedrooms, a kitchen, laundry room, common area, and more, all located on a gorgeous plot of land. With the historic charm of this timeless farmhouse and so much to do nearby, Sugar Hollow is a perfect place to enjoy quality family time.


Though temporarily closed due to COVID-19 restrictions, Monticello, home of Thomas Jefferson is a must-see bucket list stop. For a super cool twist, go on the 4th of July and see our new American citizens take part in the moving naturalization ceremony - what a great civics lesson for the kids.

Another great twist is the summer is to combine art, science and history and visit the gorgeous house, gardens and grounds. Check out the workrooms, storage areas and Mulberry row, the work hub of plantation life in Jefferson’s time. There is much to explore at Monticello, and also in the nearby area.

Michie Tavern

For a sit-down meal, just a half mile from Monitcello, enjoy lunch at this historic landmark. Servers in period garb serve classic southern fare from 11:15am -3:00pm daily all while you are immersed in notable southern culture and hospitality.


President James Monroe’s home, which he and wife Elizabeth owned for nearly thirty years, stands just three miles south of Monticello.

Highland Rustic Trails

A free adventure on the grounds of our fifth president, these trails wander through the surrounding nature. You can cover almost six miles on the four different, but interconnecting trails (yellow, blue, green and red) and they range from easy to moderately strenuous. They are also free and open to the public.

Carter Mountain Orchard

Just a couple miles from Monticello stands this lovely orchard where you can purchase some treats, pick your own fruit, and enjoy the atmosphere of this beautiful place.

James River Reeling and Rafting

Tubing on the James River is great fun, and this is a great company for your river trip. They are located at 265 Ferry Street in Scottsdale, Virginia, less than forty minutes south of Carter’s Orchard so head down from C’Ville for some tubing before dropping by the orchard on your way back. Another option is to head down to the James River for tubing and then camp the night before heading to explore Highland and Monticello on the way back.


Gathering Grounds Patisserie and Cafe

Located right in downtown Luray, this cafe offers a wide variety of gourmet sandwiches, quiche, salads, baked goods, and so much more. You’ll love this historic district cafe for breakfast, lunch, or for an on the go treat.

West Main Market

This delightful gourmet deli in the Downtown Historic District of Luray offers a great variety, and is an essential stopping point when heading off for a picnic or rafting trip.

Jordan Hollow Stables

We always have an incredible time with our kids at this stable. They are attentive to the needs and interests of all ages, from the littlest riders up. Our experiences with Lisa are always memorable - she is so personable and welcoming. We highly recommend this unique riding experience just outside of Luray on Pine Grove Road in Stanley.

New Market Rebels

For something different, bring the family to experience a minor league baseball game in New Market just twenty minutes outside Luray. The tickets are inexpensive, as are the snacks at Rebel Park.

Luray Caverns

While this is a well known tourist destination, it's a worthwhile excursion if you have school aged children. We assure those of you who may be hesitant, though you are exploring caverns, they don’t feel claustrophobic at all! Also helpful to note, if a child (or an adult) needs a bathroom break, guides are available to shuttle you out different exits at any point.

Luray Caverns also features a rope course and a maze. Conveniently located at the entrance of Shenandoah National Park, it also offers easy access to a visitor’s center and great hikes.

Enjoy the Wonders of Shenandoah National Park

Shenandoah National Park extends along the Blue Ridge Mountains in the U.S. state of Virginia. The Skyline Drive runs its length, and a vast network of trails includes a section of the long-distance Appalachian Trail. Mostly forested, the park features wetlands, waterfalls and rocky peaks like Hawksbill and Old Rag mountains. Shenandoah is home to many bird species, plus deer, squirrels and the elusive black bear.

Top Three Hikes

Near the picturesque Blue Ridge Mountains and many hiking and outdoor trails, Charlottesville is home base for families wanting to get the kids out for sunshine and fresh air.

Blue Hole in Sugar Hollow in Crozet

A 3 mile out and back family-friendly hike to a wonderful swimming hole and picnic spot. This is an all time family favorite, one that we have hiked with newborns and teens alike! There is 309 feet of elevation gain that’s proven to be manageable for children time and time again!

Parking lot address is 6796 Sugar Hollow Road

Old Rag Mountain

One of the most popular (and challenging) hikes in the Shenandoah is at Old Rag. It's a staple and often the first hike for many that live in the DC area, Richmond or even Charlottesville. The hike can be tackled via two routes. One is steep, winding and requires some boulder climbing and the other is more of an access road. The climb is well worth it and it's a wonderful place to adventure with adults, big kids and little kids (with a carrier).

It’s most appropriate for teens or children ages 8 and up with a lot of energy and athleticism. We’ve also done the hike with babies and toddlers in backpacks when eager for a challenge. The loop is 9 miles or you can do an out and back option, which is closer to 6 miles with some boulder climbing along the way. When younger kids are involved, we recommend reserving seven to eight hours for this portion. Of course, it is possible to do it faster but on this moderately strenuous adventure, you’ll want to leave plenty of time for refueling and experiencing nature.

The views are spectacular, and the hike is great fun but requires proper planning. Find preparation guidance on the NPS website. Bring plenty of water, snacks and a first aid kit and if you’re looking for a post hike stop, swing through Sperryville, Virginia. Enjoy this cute nearby town with restaurants, wineries, orchards, and The River District Arts and which is often considered the welcome center, The Sperryville Artist Cooperative.


A favorite for families with preschoolers and elementary aged children is Wildrock, located in the Shenandoah National Park just outside of Crozet with plenty of opportunities for families to explore outdoors.

Time spent outdoors lowers stress levels, builds emotional stability and fuels creativity and in our modern world with children spending on average 7-10 minutes a day outdoors and hours and hours a day on electronic gadgets, it's more important than ever to make connections with nature. Check out the trails, barn activities and more for memory making outdoor connections.

Start Driving


Skyline Drive

(An approximately 1.5 hour drive of winding roads, picnic areas, etc.)

If you’re looking for 105 miles of scenic wonder, you’ll love Skyline Drive. Running along the crest of the Blue Ridge Mountains from North to South, this National Scenic Byway and National Historic Landmark will encourage you to find all of its 70 overlooks, picnic areas, wildlife, and spanning views of the Shenandoah Valley to the west and the Piedmont to the east.

You’ll also have the option to enjoy the many hiking trails, campgrounds, and horse trails. It takes 3-4 hours to make it all the way through this scenic route at the 35 mph speed limit so pack your picnics and get ready for your adventure! Take a drive along the beautiful Skyline Drive to find yourself the most picturesque location for your picnic needs. All of them have their own special charm.

Top Picnic Areas


  • Dickey Ridge (mile 4.7)
  • Elkwallow (mile 24.1)
  • Pinnacles (mile 36.7) open year round
  • Big Meadows (mile 51.2)
  • Lewis Mountain (mile 57.5)
  • South River (mile 62.8) open year round
  • Loft Mountain (mile 79.5)
  • Dundo (mile 83.7)

There you have it! We love our town and the amenities that support our healthy and wholesome family lifestyle.

Contributing Authors: Molly Petchel, Darlene Banks, Caitlin Iseler, Randi Banks, Emily Coleman

Let us help you get outdoors with Ten Tips For Hiking Safely During COVID-19 or seek inspiration from the safety of your home in Dreaming Up Your Next Adventure. Start by Making Nature Your Focus in Harper’s Ferry, West Virginia.

To really get your imagination in motion, check out Explore the Magical Beauty of Grand Teton and Yellowstone or the recent blogs by Colin Boyd Dreaming of Safe Travel: Dry Tortugas and Why Mojave National Preserve is Our Favorite Park.

If you have a perfect getaway or a favorite landscape, please share with us at team@happyly.com. We love hearing from you!

Thoughtfully captured by:
The Team at Happyly
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