How to Plan a Multi-Generational Family Vacation to Staunton

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Summertime often means family vacation and family reunion time! If you’re looking for a destination that has something for everyone, even in a big family with diverse ages and interests, look no further than Staunton. Staunton offers a charming blend of history, culture, outdoor adventure, and family-friendly activities making it ideal for a multi-generational getaway or family reunion. Here’s our guide on where to stay, gather, eat, and play.

Where to Stay

Here are some Staunton home bases for larger groups.

• Your extended family will feel at home in Tru by Hilton, which offers comfortable rooms, free build-your-own breakfasts, and lots of communal gathering space and a game area in the lobby. Pets are welcome, and the hotel is located near the interstate and downtown Staunton. 

• Marriot Fairfield Inn and Suites boasts comfortable rooms and suites suitable for couples and families, an indoor pool, a fitness center, and free continental breakfast.
• Hotel 24 South and Conference Center is located in historic downtown Staunton. The historic structure was built in 1924, but updated and renovated in 2005 and 2018 to provide modern comforts and style. Large meeting spaces can host gatherings of up to 400 people.
• Here’s a list of more Staunton lodgings that are great for groups.

Where to Gather

Staunton has gathering spaces for groups of all sizes.

• Blackburn Inn and Conference Center is the “Valley’s most elegant and inspiring destination for weddings, meetings, retreats, and celebrations of all sorts.” Set on 80 acres, the historic inn offers a variety of gathering spaces and beautiful rooms to spend the night.
• Montgomery Hall and Gypsy Hill Park have several picnic tables and pavilions available for free on a first-come-first-served basis. Located near playgrounds and open spaces, these locations will keep the whole family entertained. Gypsy Hill Park’s Garden Center and Gymnasium can be reserved for your gathering for a fee.  
• Frontier Culture Museum also rents spaces for weddings, reunions, and other special gatherings. Choose from the pavilion, the Octagonal Barn, or the Dairy Barn and enjoy access to the museum grounds.
• Known as the Jewel of the Blue Ridge, Sherando Lake is a prime spot for a swim and a hike, but it’s also a good spot to gather a group. Snag a few picnic tables, a barbecue grill, and a spot on the sandy beach. The recreation area has bathrooms and a campground.

Where to Eat

Staunton has no shortage of restaurants serving up delicious food. Here are some of our favorites for your group.

• Kathy’s Restaurant features homestyle cooking and a breakfast menu that’s available all day. Mrs. Rowe’s is another popular pick for homestyle cooking and people rave about the pies.
• For a casual meal downtown, try the American fare at The Depot Grille or the Mill Street Grill, gourmet pizza at Shenandoah Pizza, the Southern California-style Mexican at Baja Bean Co., or head to Queen City Bistro where Southern roots and Italian vines intersect.

• BLU Point Seafood serves fresh seafood, a full menu of cocktails, and has two large private rooms for big groups.
• And don’t forget about dessert! Grab something yummy at Kline’s or Split Banana. If you want to be adventurous then grab a Belgian waffle with all sorts of toppings from Sweet Addie’s.
• Here’s a list of more Staunton restaurants good at serving groups.

Multi-Generational Fun

Easily navigable Staunton and the surrounding area shines as a destination for groups. Here are some local attractions that are good for groups of various ages.

• Take a tour through history. The Frontier Culture Museum brings the past to life with the help of costumed interpreters and hands-on activities. This open-air museum has space for young kids to run and there are paved walking paths and golf-cart transportation for visitors with mobility concerns. Woodrow Wilson Birthplace and Presidential Library also has engaging exhibits and hands-on activities celebrating the life and legacy of the 28th president. And while the space is a historic structure, most spaces and exhibits are accessible. Staunton Guided Tours can provide unique and customized walking and car tours of historic Staunton.
• Weather can be unpredictable here in the Shenandoah Valley, so if you happen to get stuck indoors don’t worry you can catch a movie at Visulite Cinemas right in downtown Staunton. Or families who want to problem-solve as a group will love working together to break out of one of the rooms at Crack the Code Escape Room.
• A few games at the Staunton Lanes bowling alley is a great way for a family to enjoy friendly competition. Kids can use bumpers and ramps on the lanes, and the snack bar caters to appetites of all ages. If pickleball is more your speed, check out the courts at Montgomery Hall Park and Gypsy Hill Park.

• August marks the 10-day Staunton Music Festival, which brings nearly 100 musicians to Staunton to perform classical music. Some concerts require tickets, but many are free! Your group will also enjoy a production of a Shakespearean or contemporary play at the award-winning Blackfriars Playhouse. Groups can also sign up for behind-the-scenes tours of the theater.
• Does your group include fans of the railroad? Staunton has plenty of places to watch the trains roll by, including the historic train station. Explore and pose for your group photos, then have everyone climb aboard a Virginia Scenic Railway excursion through the beautiful Shenandoah Valley. Younger train buffs and their adults will love a ride on the Gypsy Hill Express mini-train. 

Mobility-Friendly Hikes

If someone in your party has mobility issues or rides in a stroller, rugged hikes might be challenging. Here are some nearby accessible hikes.

• Once a resort where people came to escape the summer heat and enjoy the restorative properties of spring water, Augusta Springs Wetlands is now the site of an accessible nature trail. Flat gravel and boardwalks make up the walking surfaces and the trail features interpretive signs about the woodland creatures visitors might encounter.

• While a hike up to the top of Crabtree Falls is a tough, two-mile climb, the trail follows the falls closely and returns to offer repeated close looks. Better yet, you can reach the base of the falls (and a fine view) by a short stroll along a level, paved trail.
• The walk-a-paca experience at Point of View Alpaca Farm will charm you. You’ll pair up with a friendly (and photogenic) alpaca. Once you’re acquainted, you and your alpaca will take a guided stroll around the farm.

• Waynesboro’s paved South River Greenway runs for two miles along a Virginia Scenic River connecting four parks and natural areas.
• Groups can also sign up for a guided nature tour with Enchanted Nature Tours. Experienced naturalists lead adventures specifically designed for your interests and abilities.
• Your entire party will love spending time in Shenandoah National Park. Choose from hundreds of miles of trails or ride along the Skyline Drive enjoying the scenery and stopping at the overlooks for nature viewing and picnicking.

Hopefully, you now know where to gather and how to keep your multi-generational family busy on your trip to Staunton!