Best Things to Do in Chesterfield, Virginia: A Weekend Getaway Guide

If you are a traveler looking for a unique and off the beaten path Virginia weekend escape, then look no further than Chesterfield County. While it may not receive as much attention as some of the state’s better known destinations, this charming corner of Virginia has so much more to offer travelers than they might expect. With its local arts scene, creative dining experiences, live entertainment and one of the most unique zoos in Virginia, Chesterfield is a perfect destination for anyone seeking a getaway brimming with variety and a few surprises. Located about two hours from Washington, DC, it is also an easy road trip for a quick change of scenery. Here is everything you need to know to plan the perfect weekend trip exploring Chesterfield County, Virginia.

The Perkinson Center for the Arts & Education

My first stop was the Perkinson Center for the Arts & Education, a community arts center with a gallery, classrooms and a beautiful Theater. During my visit I checked out the current  gallery on display called  tiny works…BIG IMPACT!, a community exhibition featuring small scale pieces from 58 local artists ranging from preschool aged creators to experienced professionals. The exhibition runs from July 22 through September 11, 2026 and is definitely worth stopping in for a look!

I also got a peek inside the theater and stage, and it was strikingly beautiful—an intimate 350-seat space with modern lighting and acoustics designed to make every seat feel close to the performance. Named for country music legend Jimmy Dean, the venue hosts a 2026 season featuring a mix of concerts, comedy acts, and community theater productions—be sure to check their calendar for upcoming shows and dates.

NAPA Kitchen & Wine: Garden Party

For dinner, I visited NAPA Kitchen & Wine, a California inspired restaurant and wine bar located at Westchester Commons. The seasonal Garden Party pop up had transformed the space with florals, greenery and colorful themed details, making dinner feel like a full experience rather than simply another meal out.

NAPA Kitchen & Wine offers a diverse menu featuring fresh sushi, shareable plates, and a curated selection of wines. The restaurant focuses on seasonal flavors and well-crafted dishes that pair perfectly with their drink offerings. The Garden Party is a seasonal experience, and reservations are highly encouraged while the pop up is available. NAPA also offers happy hour Monday through Friday from 3 to 6 p.m., with specials on select cocktails, sushi rolls and oysters.

Westchester Concert Series

After dinner, I walked over to the Westchester Concert Series and caught a live performance by The KOS Band. This free summer concert series brings local bands to the Main Street Stage at Westchester Commons, with plenty of space to set up a chair, enjoy food from the surrounding restaurants and dance once the music gets going. The crowd had an incredible energy with people of all ages up on their feet and dancing, this event is an absolute blast. 

The 2026 series continues on select Thursdays from 5:30 to 8:30 p.m. Upcoming performances include Josh Duncan Band on August 6, Brasswind on August 20, Funhouse on September 3, Skip Castro Band on September 17 and En’Novation on October 1.

If you plan to attend, bring a chair or blanket. Food purchased from nearby Westchester Commons restaurants is allowed inside, but outside alcohol and drink containers are not permitted. Adult beverages are available for purchase, with proceeds benefiting a different local nonprofit at each concert. 

TIFA Chocolate & Gelato

I ended the evening with dessert at TIFA Chocolate & Gelato, which is also located at Westchester Commons. I ordered strawberry and lemon gelato, and both flavors were delicious, especially together. This is a sweet treat that is certainly NOT to be missed!

TIFA serves more than two dozen handcrafted and rotating gelato flavors, along with artisanal chocolates, pastries, coffee and specialty drinks. The Midlothian location is currently open until 10 p.m. Sunday through Thursday and until 11 p.m. on Fridays and Saturdays.

Metro Richmond Zoo

I dedicated the second day of my trip to Metro Richmond Zoo, which ended up offering much more than the traditional zoo experience. Spread across 150 acres, the zoo is home to approximately 2,000 animals representing 190 species. This makes it Virginia’s largest zoological park based on the number of animals.

One of the most memorable parts of my visit was participating in two private animal experiences. During the Galápagos Tortoise Experience, I learned about the world’s largest tortoise species, touched their shells and even got to feed them. I also did the African Penguin Experience, which brought me inside the penguin habitat for an up close encounter where I learned more about their behavior and current conservation efforts.

Both animal experiences last approximately 30 minutes and currently cost $50 per person. Advance reservations are required so be sure to book in advanced!

Even without booking an animal encounter, there is plenty to fill the day. The Safari Train travels through an eight acre habitat that cannot be explored on foot, while the Safari Sky Lift offers sweeping views over the zoo. For more adventure, Treetop Zoofari takes you above the grounds on zip lines and aerial obstacles. You can also feed giraffes, join a daily keeper talk and explore the rides and play areas throughout the park.

The zoo is open Monday through Saturday from 9:30 a.m. to 5 p.m. and is closed on Sundays. General admission currently costs $27.95 for adults, $26.95 for seniors and $20.95 for children ages 2 through 11. The Safari Train and Safari Sky Lift each cost an additional $4 per rider.

From local art and creative dining to live music, gelato and memorable wildlife experiences, Chesterfield offers plenty of ways to fill a weekend. Whether you follow this entire itinerary or select a few favorite stops, this often overlooked Virginia destination is well worth adding to your travel list. Visit the official site for Experience Chesterfield for more travel inspo and overnight accommodation options!

This blog post was part of a hosted visit and paid partnership with Experience Chesterfield. Recommendations and reviews remain genuine, these opinions are my own.

Check out Stays and Getaways IG for the video feature covering this entire getaway itinerary!

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