A Weekend to Wander

Photo: Darnell Pumpkins

A Weekend to Wander 

Autumn leaves are content to wander, enjoying every moment in flight. We’ve noticed visitors doing the same. Whether they’re savoring sunset picnics or runaway licks of ice cream, people are embracing the WanderLove spirit. While the days are shorter, Orange County lengthens the fun as we turn the page to October. In celebration of a crisp new season, here’s a Weekend to Wander itinerary for your enjoyment.


Photo Credit: Liberty Mills Farm Facebook

Start your day in Somerset at Liberty Mills Farm, featuring panoramic views of autumn’s abundance. Opening for the 2021 season, Saturday, September 11th!

Home to the largest corn maze in the US, Liberty Mills is a great place to linger. Each year, Liberty Mills creates a new concept for its 34-acre maze. This year’s theme is “America the Beautiful.” Flashlight nights and fire pits to enjoy the maze under the stars. Family bucket list worthy for 2021!

A trip to Somerset calls for a lunch stop at the Market at Grelen. Take a snap at the LOVEworks sign, surrounded by seasonal blooms. Grab a gourmet sandwich and a scoop of caramel apple ice cream to enjoy on the patio.

Fall colors blaze at our wineries, in sync with the local harvest. Trellised patios and cozy tasting rooms are made for “sweater weather”. To completely unplug, book a private tour with Central Virginia Wine Tours for up to six in a Cadillac Escalade. Meander through the foothills, visiting up to five wineries in an afternoon. When your day draws to a close, the tour company will arrange a meal to remember.

When you’re ready to wind down, Orange County’s bed and breakfasts and inns call you home. Watch the sunset with a warming cocktail from the Mayhurst Estate’s English-style gardens or their fairy-tale gazebo cap off the perfect day.


Photo Credit: The Light Well Restaurant Facebook

Kick off the morning with a heart-pumping hike through Seigen Forest. This 170-acre trail network is flanked by foliage and Rapidan River views. The Blue Trail, running ¾ mile in each direction, rewards hikers with vistas over the bluffs. 

Old Bay Bloody Marys and pesto eggs beckon at The Light Well Restaurant in Orange. The winners of a 2020 Trip Advisor Travelers’ Choice Award, The Light Well infuses southern hospitality into every dish.

Walk off brunch in downtown Orange. Lovingly landscaped trees and seasonal window displays encourage strolling at an easy pace. If you’re souvenir shopping, Grelen Downtown or Finders Keepers specialize in locally-crafted gifts and antiques. And if you’re in search of the elusive great pumpkin (or pumpkin-flavored bakery treat), you may very well find it at Darnell’s Garden Patch.



From vineyard to woodland, our backdrop inspires relaxation and quiet contemplation. Whether it’s a well-loved bench overlooking the mountains or a fireside wing chair, Orange County welcomes your WanderLove.