A Local’s Guide to Fall in Richmond & Midlothian, VA

There is a reason we look forward to fall in Richmond all year.

The humidity finally gives us a break, patios become the place to be again, the trees along the James begin to change, and suddenly spending an entire Saturday outside sounds like a very good idea.

And you really don't have to go far to make the most of it.

Whether you're looking for a quiet walk followed by a great lunch, pumpkins with the kids, a winery afternoon with friends or a day in the city that ends with cocktails, we've rounded up some of our favorite ways to spend fall around Midlothian, Chesterfield and Richmond, with a few worthwhile drives just outside the area.

Think of this as less of a checklist and more of a collection of fall days worth having.

1. Walk Robious Landing, Then Grab Lunch in Midlothian

Start: Robious Landing Park
Then: Lunch or drinks at Tazza Kitchen
Best for: An easy Saturday or Sunday close to home

If you live along the Robious corridor, Robious Landing is one of those places that's easy to forget is practically in our backyard.

The 102-acre park sits directly on the James River and includes wooded trails, river access and picnic areas. Fall is one of our favorite times to visit, especially once the trees along the river begin changing.

A portion of the riverfront trail is currently closed because of erosion, so check Chesterfield County's park updates before heading out, but there are still other areas of the park to enjoy.

Afterward, head to Tazza Kitchen at Alverser Plaza. Wood-fired pizza, a good cocktail and fall patio weather make for a pretty great reward after a morning outside.

LOCAL TIP: Go to Robious Landing earlier in the day when the trails are quieter, then make lunch your second stop.

2. Explore Midlothian Mines Park, Then Spend the Afternoon in the Village

Start: Midlothian Mines Park
Then: Explore the Village of Midlothian
Finish: Dinner at Oceano
Best for: A relaxed Midlothian date day

If you've driven past Midlothian Mines Park countless times but haven't stopped, fall is a good time to finally do it.

The park combines walking trails and wooded scenery with a piece of Midlothian history that many people living here don't realize is so significant. The area's coal-mining roots date back centuries, and the park preserves part of that history alongside an easy outdoor walking area.

After your walk, spend some time around the Village of Midlothian before heading to Sycamore Square for dinner at Oceano. The seafood-focused restaurant feels a little more special than an everyday lunch stop, making this a good itinerary for a fall date afternoon that turns into dinner.

3. Pick Pumpkins at Chesterfield Berry Farm

Start: Chesterfield Berry Farm in Moseley
Then: Take the scenic way back through western Chesterfield
Finish: Triple Crossing in Midlothian
Best for: Families, groups of friends or anyone committed to doing fall properly

A grocery-store pumpkin works just fine, but wandering through an actual pumpkin patch feels considerably more like fall.

Chesterfield Berry Farm's 2026 pumpkin season brings back the farm's fall activities, including pumpkins, a corn maze, farm animals and family activities.

And here's where we'd make it a full afternoon rather than simply driving home afterward.

On the way back toward Midlothian, stop at Triple Crossing's Midlothian location at Winterfield Crossing. Their outdoor beer garden overlooks the pond, and you can pair a beer with one of their Neapolitan-style pizzas.

Pumpkins, a country drive, pizza and a beer outside. That's a solid October Saturday.

4. Spend a Fall Day at Pocahontas State Park

Start: Pocahontas State Park
Explore: Beaver Lake or one of the park's trails
Optional stop: Spring Run Vineyards
Best for: A full outdoor day without leaving Chesterfield

Pocahontas State Park is one of the best reminders of just how much outdoor space we have close to Richmond.

Located in Chesterfield County, the park has three lakes and roughly 90 miles of trails, which means this can be anything from an easy walk to an entire day outside.

Fall is particularly beautiful around the lake as the hardwood forest begins changing color.

For something different afterward, check the schedule at Spring Run Vineyards in Chesterfield. This small farm winery hosts seasonal gatherings, markets and live music on select days, so it is worth planning your park day around one of their fall events.

LOCAL TIP: Don't try to "see Pocahontas" in one visit. Pick one section and slow down. That's half the point.

5. Make It a Winery Day in Goochland

Start: Take the back roads west
Visit: Byrd Cellars or Elk Island Winery
Optional: Add another stop along the Goochland Craft Beverage Trail
Best for: Couples, friends and an adults-only fall afternoon

You don't have to drive all the way to Charlottesville to have a Virginia wine-country day.

Head west of Short Pump and Midlothian into Goochland, where the landscape quickly opens into rolling countryside, farms and vineyards.

Goochland's craft beverage trail now includes multiple wineries, breweries, a cidery and a distillery.

For a traditional vineyard experience, try Byrd Cellars, a family-owned winery in Goochland, or continue west to Elk Island Winery along River Road. Elk Island is a smaller farm winery and an especially nice choice if you're looking for something quieter than the larger Charlottesville wineries.

This is also one of those days when we recommend taking the slower route. Fall in Goochland is part of the experience.

LOCAL TIP: Winery hours can be limited, particularly later in the season, so always check before leaving home.

6. Or Make the Drive to New Kent Winery

Destination: New Kent Winery
Order: A Virginia wine flight or guided tasting
Stay for: The vineyard views and something from the small-plates menu
Best for: A fall date, girls' afternoon or visiting friends

If you want more of a destination winery experience, head east instead.

New Kent Winery offers daily wine flights and guided tastings, along with Talleysville Brewing Company onsite for anyone who would rather have a beer. The property has an expansive porch and patio overlooking the vineyards, which is exactly where we'd want to be on a crisp October afternoon.

They also serve small plates, so there's no need to rush off for lunch.

Check their events calendar before going. Live music and other special events are regularly scheduled, and they already have fall 2026 programming beginning to appear on the calendar.

7. Walk Maymont, Then Head to Carytown

Start: Maymont
Then: Walk and shop Carytown
Eat: Can Can Brasserie, East Coast Provisions or Lolita's
Best for: Showing an out-of-town guest why we love Richmond

This might be one of the most "Richmond" days on the list.

Start at Maymont and give yourself plenty of time to wander. The 100-acre property is beautiful throughout the year, but the Japanese Garden and mature trees make October particularly special.

From there, head toward Carytown.

Walk the shops and then decide what you're in the mood for. Can Can Brasserie is a Richmond staple if you want a leisurely French café atmosphere. East Coast Provisions is a good choice for oysters, seafood, sushi and cocktails. Lolita's is on of our personal Carytown favorites, with incredible Mexican food, wonderful service and some of the best margaritas in Richmond. Their daily Happy hour is especially worth a stop, with specials on drinks and some of our favorite items from the menu. 

8. Catch Sunset at Libby Hill, Then Head to Blue Atlas

Start: Libby Hill Park
Then: Take a short drive to Blue Atlas in Fulton Hill
Best for: Date night, dinner with friends or showing off Richmond to out-of-town guests

Save this one for a clear fall afternoon.

Head to Libby Hill Park with enough time to wander through Church Hill before sunset. From the overlook, you'll get one of Richmond's most recognizable views of the James River, and by late October, layers of fall color make an already beautiful view even better.

Once the sun goes down, make the short drive over to Blue Atlas Restaurant & Market in Fulton Hill. Set inside a historic schoolhouse, Blue Atlas has become one of Richmond's more unique dining spots, with a globally inspired, seasonally changing menu designed around dishes that are perfect for sharing.

The setting is just as much a reason to go. Outdoor seating includes a covered portico and lower patio, with beautiful views toward the Richmond skyline. If the weather cooperates, it's an especially good place to settle in with a cocktail or bottle of wine and order several plates for the table.

Going a little earlier? Blue Atlas also offers happy hour Wednesday through Friday from 3 to 6 p.m., making this an easy stop before or after exploring the neighborhood.

LOCAL TIP: Dinner reservations are recommended, particularly when the weather is nice and you're hoping to sit outside.

9. Walk Pony Pasture, Then Head West for Dinner on River Road

Start: Pony Pasture
Then: Take a scenic drive west along River Road
Finish: Portico Restaurant & Bar
Best for: A fall date, leisurely Sunday afternoon or dinner with friends

Few places feel more quintessentially Richmond than Pony Pasture on a beautiful fall afternoon.

Walk the wooded trails along the James, find a spot near the rocks or simply take your time by the water. Once the leaves begin changing, the mix of river views, exposed rocks and colorful trees makes this one of our favorite places to enjoy fall without ever leaving Richmond.

When you're ready for dinner, skip downtown and head west toward River Road.

Portico Restaurant & Bar is a perfect follow-up. Tucked into a charming cottage on River Road, Portico feels almost like you've left Richmond for the countryside. The restaurant serves an Italian-inspired menu along with wine and cocktails, but the setting is what makes it especially good for fall. Its outdoor stone terrace is surrounded by gardens, with a large stone fireplace and a cozy atmosphere that feels made for a crisp evening.

If the weather is nice, request a table outside and give yourself time to enjoy it. This is not the stop we'd rush through.

LOCAL TIP: Take River Road instead of the highway on your way to dinner. It's a prettier drive, especially once the leaves begin changing, and makes the whole afternoon feel like one continuous fall outing.

10. Walk Hollywood Cemetery in the Fall

Start: Hollywood Cemetery
Take your time: Explore the historic grounds and James River overlooks
Then: Head into the Fan
Finish: Wine at Jardin
Best for: History, architecture and something a little different

Hollywood Cemetery isn't an obvious "fall activity," which is exactly why we like including it.

The historic grounds sit high above the James and are filled with mature trees, winding roads, monuments and some unexpectedly beautiful river views. Virginia tourism specifically highlights Hollywood Cemetery as a place to experience Richmond's fall foliage.

Afterward, head into the Fan and settle into Jardin.

Part wine shop, part wine bar, Jardin has a garden and patio that make it particularly appealing while Richmond is still enjoying those perfect in-between temperatures.

It's a very Richmond combination: history, architecture, trees and wine.

11. Spend an Afternoon at Lewis Ginter Botanical Garden

Start: Lewis Ginter Botanical Garden
See: The new gardens, Wick Lake and Conservatory
Then: Stay for a leisurely afternoon nearby
Best for: Families, garden lovers and visiting parents

Lewis Ginter has even more to see in 2026.

Following its major expansion, the Garden now includes more than seven acres of new gardens, an expanded Conservatory, Wick Lake and a year-round butterfly exhibit.

In fall, the changing foliage around the gardens and water adds another reason to go.

Give yourself a few hours rather than rushing through. This is one of the easier options on the list for a multi-generational outing when you want to be outside without hiking.

14. Spend a Fall Afternoon at a Richmond Brewery

Try: Hardywood Richmond
Or: The Veil in Scott's Addition
Add: Buskey Cider for something especially seasonal
Best for: Groups of friends and casual fall afternoons

Richmond's craft beverage scene deserves its own fall afternoon.

Hardywood's Richmond location has a large outdoor beer garden, making it an easy choice when the weather is good. Scott's Addition gives you even more options within a relatively small area, including The Veil and Buskey Cider.

And if there is ever a season made for a local cider, this is probably it.

Fall Is a Good Reminder to Explore Your Own Backyard

One of the things we love most about living and working in the Richmond area is how different life can look within a relatively short drive.

You can spend the morning beside the James in Midlothian, have lunch in the city, sip Virginia wine overlooking a vineyard the next afternoon and still be home in time for dinner.

And that's also why we believe knowing Richmond real estate requires more than knowing home values and ZIP codes. It's understanding what it actually feels like to live in these communities, from the restaurants around the corner to the trails you walk on Saturday morning.

So get outside, order something good, take the scenic route and enjoy fall while it's here.

And if all that exploring has you curious about a new neighborhood, we'd be happy to show you around.

Tina Morris & Co.