Sep 17, 2022 - Things to Do

10 must-do fall activities in and around Richmond

view from skyline drive in shenandoah national park

The view from Skyline Drive in the Shenandoah National Park. Photo: Karen Bleier/AFP via Getty Images

Pumpkin spice lattes are back, which means it's time to work on your fall bucket list. Here are some ideas to get you started.

1. Go apple picking at Carter Mountain Orchard.

The family-run orchard has been around for more than 100 years, with U-pick peaches and apples. After your apple-picking adventure, grab some apple cider doughnuts from the country store and get a slushie from the Bold Rock taproom.

  • Apples are available mid-August through November. You can find the varieties currently available here.
  • Details: The orchard is open 9am-6pm daily, and tickets are required on peak fall weekends. You can buy them here.
  • Address: 1435 Carters Mountain Trail, Charlottesville.
Carter Mountain Orchard
Photo courtesy of Carter Mountain Orchard

2. Hoist a stein at St. Benedict Oktoberfest.

Expect German cuisine, music and dancing, Christkindlmarkt, children's activities and lots of beer.

  • The festival runs Sept. 16-18 at 300 N. Sheppard St.

3. Or eat schnitzel at Bier-Garden.

The two-night, Bavarian-style festival features steinholding, live music, polka, lots of beer, German foods and kids' activities.

  • The festival runs Sept. 23-24 at Maymont (1000 Westover Road).

4. Go leaf peeping at Shenandoah National Park.

Drive along Skyline Drive or hike one of the many routes that make up the over 500 miles of Shenandoah trails. Some ideas include:

Map out your adventure here.

shenandoah mountain leaves changing color
Photo: Karen Bleier/AFP via Getty Images

5. See DJ Grandmaster Flash at 2nd Street Festival.

Celebrate the historic Jackson Ward neighborhood with the 34th annual festival Oct. 1-2. Expect kids' activities, food vendors, live performances and an antique car show.

  • Find parking and a full event map here.

6. Pick a pumpkin.

There are plenty of patches to choose from, including:

pile of pumpkins
Photo: Amy Sussman/Getty Images

7. Attend the Richmond Folk Festival.

For the 18th year, the Richmond Folk Festival promises five stages with performances from artists around the world. Expect more than 30 vendors serving up international cuisine, from Caribbean jerk chicken to Filipino adobo.

  • The free festival runs Oct. 7-9.

Read our full fall arts guide.

8. Lean into spooky season with a haunted attraction.

From haunted amusement parks to ghost tours, here are some frightening festivities:

9. Head to Hanover Avenue for trick-or-treating.

Put on your best costume and stroll around the 1900 block of Hanover Avenue with hundreds of other Halloween fanatics.

  • Other trick-or-treat spots include the Church Hill and Oregon Hill neighborhoods.
  • Or attend the All Saints Theater Company's 17th annual parade.

10. Vineyard hop along the Monticello Wine Trail.

Romanticize your life and spend a day sipping wine while overlooking rolling hills covered in fall leaves. Some options include:

Jefferson Vineyards: Virginia's first wine company might be a good place to start your wine tour. Sip a flight al fresco surrounded by gardens.

  • Hours: 11am-6pm Wednesday-Sunday.
  • Address: 1353 Thomas Jefferson Parkway, Charlottesville.

Pippin Hill Farm & Vineyards: For elevated cuisine and some of the most beautiful views, head to this popular winery.

  • Hours: 11am-5pm daily (closed the first Monday of each month).
  • Address: 5022 Plank Road, North Garden.
pippin vineyard
Photo: Sera Petras Photography

Glass House Winery: This boutique winery has a unique tropical (and very Instagrammable) greenhouse-like setting.

  • Hours: 12-5:30pm Wednesday-Thursday, 12-9pm Friday, 12-8pm Saturday, 12-5:30pm Sunday.
  • Address: 5898 Free Union Road, Free Union.

See all 40 vineyards and wineries on the trail here.


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