The half-mile Dragonfly Loop at the Webb Nature Sanctuary is perfect for little ones. 

1. Webb Nature Sanctuary

On our day trip adventure we started with a short hike around Webb Nature Sanctuary. Open from dawn to dusk, this 20-acre park includes a variety of habitats such as meadows, streams, and woodlands. Follow the Dragonfly Loop for a half-mile scenic stroll through the sunny meadow surrounded by wildflowers, the shady fern-covered stream area, and the tall trees of the woodlands. My kids enjoyed chasing each other and traipsing down the stream bank to the river. Parking is free and outside the main entrance—just make sure to avoid parking on the private property next to the park.  

 
There are so many yummy choices at Peterson's Ice Cream Depot.

2. Peterson’s Ice Cream Depot

After a hike, you might be ready for some lunch or ice cream. Peterson's, which made our list of the best ice cream shops near DC, serves up a great selection of homemade hard and soft-serve ice cream flavors. We loved the chocolate and mint chip! The regular food menu offers delicious fries, chicken sandwiches, and loaded hot dogs with lots of yummy toppings. The ordering and seating areas are all outdoors, and kids can play board games like Connect 4 while they wait. Peterson's is open on Saturdays and Sundays from noon to 8:30pm through November 8.

Grab a casual meal at Clifton Cafe. Photo courtesy of Elizabeth J., Tripadvisor

3. Clifton Cafe

Another option for a casual meal is the historic Clifton Cafe. Best known for its savory or sweet crepes, Clifton Cafe’s diverse menu also includes breakfast items like pancakes and waffles and lunch and dinner items such as sandwiches and salads. There's also a kids' menu with items such as mac and cheese and PB&J sandwiches, and seating is available both indoors and outdoors. 

4. Trattoria Villagio

If you're looking for a sit-down meal that's a bit less casual but still kid-friendly, this popular Italian restaurant is the perfect choice. It's got a gorgeous outdoor patio heated by fire pits in the winter, plenty of indoor seating, and a kids' menu that offers child-sized portions of grilled salmon and filet mignon along with more traditional choices like spaghetti and chicken tenders. Kids—and grown-ups—will also love the large selection of New York-style pizzas!

 
There is lots for kids to explore at the Clifton Town Park playground.

5. Clifton Town Park

After your meal, you can walk to the adorable playground at Clifton Town Park. Kids can enjoy big climbable trains and trucks, swings, a four-seater teeter-totter, a basketball court, a wooden play structure, and plenty of room to run.  

6. Historic Homes

Since you're already on Clifton's old-fashioned Main Street, take a stroll up and down the street and its side streets—including Chapel Street, Chestnut Street, and School Street—to check out all of the town's historic houses. The houses have signs out front that describe their history and interesting facts about them. See if you can find the house where the "Sleepless in Seattle" screenplay was written and the one that was once home to a Titanic victim. 

Take a peek inside an old-fashioned red caboose at Historic Devereaux Station. Photo courtesy of the Historical Marker Database

7. Historic Devereaux Station Caboose

The Union Army commissioned Devereaux Station during the Civil War on the Orange and Alexandria Railroad line in 1863. In 1868, a passenger station was built and its name was changed to Clifton Station. Today, a red train caboose from that time period stands at the site of the station. Kids love to climb the stairs of the caboose and have a peek inside. 

 
Pack a picnic and take the whole family to Paradise Springs Winery. Photo courtesy of djfowler, Tripadvisor

8. Paradise Springs Winery 

With its expansive lawn and plenty of outdoor seating, Paradise Springs made our list of eight kid-friendly wineries near DC. Outside food is allowed with the purchase of wine, so bring a picnic lunch and enjoy a wine tasting while the kids play tag or just run around. Children are not allowed in the winery's bar area, but they are welcome outdoors, as are leashed dogs.

 
Immerse yourself in nature at Hemlock Overlook Regional Park. Photo courtesy of Famartin, Wikipedia

9. Hemlock Overlook Regional Park

Next to the winery is the entrance to Hemlock Overlook Regional Park, which is home to lots of tall trees and well-maintained trails. If you walk west from the parking area, you can take the Yates Ford Trail down to the Bull Run-Occoquan Trail, which goes along the Bull Run stream. Or, you can head north from the parking area to the Union Mills Trail, which also leads to Bull Run. Union Mills Trail is longer, but both trails are under a half-mile one way.  

All photographs, unless otherwise indicated, were taken by Bob Sivinski.