Richmond Revealed: The Ultimate Guide To The City’s Best Spots

Are you looking for a great place to visit for a weekend getaway with the guys (or the family)? I’ve got an amazing spot that’s probably not on your radar – Richmond, Virginia. The capital of Virginia, Richmond was just named as the #1 town in America to visit by CNN Travel, and after spending a few days exploring the area with some friends, I can totally see why!

Now I’ll be honest, when my buddy James from ManTripping first hit me up with the idea of going to Richmond, I was a little hesitant, as I naturally associated Richmond with history (after all, it is among America’s oldest major cities), and that’s not really my thing. But after doing some research, I discovered that Richmond (RVA) has a LOT more to offer, including an amazing foodie scene, wineries, festivals, outdoor activities, and more.

While I could have flown into Richmond International Airport, I discovered that it was only a 4.5-hour drive from Philadelphia, so I packed up my Ford Maverick and hit the road. Having driven through Virginia many times before, I knew that it would be best to leave early, since Beltway traffic can get pretty crazy during the afternoon and evening hours.

We stayed at the Quirk Hotel, a charming boutique hotel located in the heart of downtown Richmond, off of Broad and Jefferson. Originally erected in 1916 as the J.B. Mosby & Co. Dry Goods Store, this Italian Renaissance-designed building became Quirk Hotel in 2015, and they’ve worked to embrace the legacy and location of the hotel while creating a whimsical, artful environment for their discerning guests.

Each of the 73 guestrooms has been outfitted with custom bed frames crafted from 100-year-old Virginia walnut beams that were taken out of the original structure and repurposed during construction. They also feature segmental arches, jaw-dropping floor-to-ceiling windows, and groin vault ceilings. The rooms are massive, and it really is a room fit for a king (or queen).

If you stay here, you absolutely must check out the Q Rooftop Bar, a 2,000 sq-ft open-air bar that offers gorgeous views of the Richmond skyline, while serving up a creatively curated menu of drinks and Belgium inspired beer garden fare. The Q Rooftop Bar is open 5-11pm daily, weather permitting.

After getting a good night’s sleep, we headed out bright and early Thursday morning to the Keystone Truck & Tractor Museum in Colonial Heights, VA. Let me tell you, nothing could have prepared me for this place. This is the largest tractor museum in the world, with 125,000 square feet of fully restored antique farm tractors, farm related equipment, antique road trucks, classic cars, motorcycles, vintage gas pumps, and more!

While I’m more of a car guy, I have an appreciate for all things gas-powered, and it was wild seeing all of these fully restored vintage tractors. And in addition to all of the tractors, cars, and bikes, they also had a pretty amazing collection of oil cans, automotive signage, clocks, and advertising posters of yesteryear, the kind of stuff they’re always looking for on American Pickers. We probably spend a good 2.5 hours here, there’s just so much to take in. A visit to Keystone is an experience you won’t soon forget.

From there, we headed over to Jolene Family Winery in Quinton, VA for a little wine tasting, me getting a flight so I could try a bunch of their different offerings, followed by lunch in one of their unique Lakeside Lounge Tents (we got a bunch of food from Ukrops and it was all so delicious.. I’m still thinking about those amazing chocolate mini pies).

As if that wasn’t enough, after lunch we decided to hit up New Kent Winery & Talleysville Brewing Company for some more drinks, because why not? They had a great selection of Virginia wines and seasonal brews, along with some small plate food selections. I grabbed a beer and sat on the patio overlooking their beautiful vineyard, enjoying a little “me time” before we headed back to the hotel.

For dinner, we had to try L’Opossum, a highly recommended restaurant that offers up playful, sophisticated spins on French cuisine and craft cocktails in an eclectic, art-filled space. The menu certainly gave me a chuckle, with tongue-in-cheek drink and dish names (eg. “Vegan Orgy On Texas Beach”, “Filet Mignon of Beef Swellington”, etc).

Everyone at the table ordered different things, and there honestly wasn’t a bad dish among us. I LOVED my Beef Swellington (a deconstructed Beef Wellington, crowned with a fascinator of truffled duxelles aux champignons et cognac, in a pink peppercorn & port reduction), and it’s honestly a pretty genius way to make the dish. Apps, drinks and dessert were equally great. A solid choice for sure, setting the bar high for the rest of the trip.

On Friday morning, we checked out a couple of museums, starting off at the Science Museum of Virginia. While I’m not usually one for museums, this place was seriously cool, and I only wish that we had more time there. They had a massive SR-71 Blackbird supersonic jet on display (hanging from the ceiling), a bunch of NASA stuff, a steampunk exhibit, a booth where you can feel hurricane force winds, a robot you can play air hockey against, and much more.

From there, we went to the Virginia Museum of History & Culture, where you can dive into Virginia’s rich past with exhibits spanning from prehistoric times to the present, providing a comprehensive look at the state’s cultural heritage. The VMHC has a collection of more than 9 million items (but not all of them may be on display to the public), it’s really amazing. They also had a Julia Child traveling exhibition, which was pretty interesting as well.

Later that afternoon, we did a Riverfront Canal Cruise, floating along downtown Richmond’s historic Canal Walk and reviewing centuries of Richmond’s history, from Powhatan’s Chiefdom to the first commercially successful electric streetcar in the world, all while traveling in authentically styled canal boats. We got to see the unique Triple Crossing railroad, tobacco warehouses that have been converted into trendy lofts, the Virginia Capital Trail, the Low Line gardens and James River wildlife. All this in just 40 minutes.

That night, we went to the annual Riverrock outdoor sports and music festival, and there was something for everyone there. From tunes to trail running, bikes to bouldering, SUPs to pups, fishing, craft brews, paddling on the James, and more. They also have a variety of food trucks and vendors on site. If this sounds like your kind of thing, you definitely want to hit this up next year (May 16-18, 2025).

I woke up bright and early on Saturday morning, excited for the NASCAR Racing Experience at Richmond Raceway that I was scheduled to do. Sadly, Mother Nature had other plans, as it was raining hard. Needless to say, this experience was cancelled, and I was super bummed, as I was stoked to drive a NASCAR race car on a racetrack at speed. 🙁

But we made the best of a bad situation, getting a VIP tour of Richmond Raceway, and we even did a lap on the track (in a Toyota Camry). Since it was still raining, we didn’t go fast at all, but it was cool nonetheless. I wouldn’t mind coming back here for one of the NASCAR races in the future, as it’s a pretty sweet track.

Afterwards, we drove to downtown Ashland, eating lunch at Iron Horse Restaurant, which serves “new modern Southern” food. Once again, everything was delicious, from the shrimp and grits to the jumbo soft pretzel to the pulled chicken BBQ sandwich. Nothing fancy, but all super tasty and reasonably priced.

While it would have been nice to explore this quaint little town, the rain kind of put a damper on things. We did check out the Secretariat statue, and we got to see the train that runs right through the center of town. And we might have stopped at a local brewery for a quick drink. Then we headed back to the hotel for a little R&R before dinner.

Saturday night’s dinner reservations were at Lillie Pearl, a full-service restaurant serving New American cuisine with southern ingredients and global influences. The place had a cool vibe, great music playing overhead, and a tantalizing menu. we started off with the baked mac and cheese (amazing!) and roasted heirloom baby carrots (insane!), and for my meal I went with the braised short ribs. For dessert, I got Millie’s banana pudding, which was out of this world.

Honestly, there are no bad choices on this menu, everyone in our party got different entrees (fried chicken, pork chop, lamb shank), and they all were amazingly delicious. Needless to say, the next time I visit Richmond, Lillie Pearl will definitely be my first stop!

Sunday was our final day in town, and we started things off with breakfast at Perly’s, a popular Jewish restaurant and deli in town. There was a long line of people waiting even before they opened, so clearly this was the place to be for people in the know.

Their brunch menu had my mouth watering, but I finally decided on French Toast (Cinnamon Babka French Toast w/ maple syrup, stewed apples, golden raisins & pecans) and a chocolate egg cream. Both were spectacular! I got a black and white cookie for later, and it too was great.

Then we headed off to Maymont, a 100-acre historic estate overlooking the James River that was given to the public by James and Sallie Dooley, who lived there from 1893 to 1925. Today, Maymont is a welcoming community gathering place, with many unique experiences for all to enjoy, including the historic Maymont Mansion, The Robins Nature Center, an arboretum, formal gardens, and habitats for native Virginia wildlife and farm animals.

Maymont serves over 700,000 guests annually, with free admission to the grounds, plus guided and self-guided tours. It’s an absolutely sprawling estate, and we only scratched the surface during our limited time there, but I know that I’ll definitely be coming back.

Last but not least, we wrapped things up with the RVA Historic Trolley Tour, which is great for the history buffs out there. Travel through a rich narrative of 400 years of history in one of the most fascinating and oldest cities in America. See the sights and learn about Richmond’s landmarks, riverfront, architecture and history, all aboard a classic air-conditioned trolley. At nearly 2 hours long, it’s a pretty comprehensive tour.

As you can see, Richmond Virginia has a whole lot to offer, making it a great destination for your next weekend trip, bachelor party, family vacation, or whatever. A huge thanks to Visit Richmond VA for bringing us out to experience this amazing region for ourselves, and I can’t wait to come back and visit again.