Local’s Guide to Fall Fun in Ashland

August 31, 2020

Editor’s note: Call destinations before you visit to make sure they’re open. Stay posted on what Oregon’s phased reopening means for you, and follow these steps for social distancing outdoors. Also, remember to bring your face covering, required for all of Oregon’s public indoor spaces and outdoors when keeping 6 feet of distance isn’t possible. Here’s what to know about Oregon’s outdoors right now.

Craving sunny skies, arts and culture and exquisite wine-tasting in wide-open spaces? There’s plenty to do in Ashland, for Oregonians who live close by. If you do visit, make the trip only when you feel safe to travel and make an extra effort to show kindness to local businesses and communities while things are constantly changing during COVID-19. Downtown Ashland has closed part of its plaza to traffic and converted parking spaces into spots for outdoor dining, to make more room for people to socially distance while shopping and exploring on foot. If you find yourself in Ashland this fall, here’s what to do in town. 


Shop, Dine and Sip Local

The city of Ashland is inviting visitors to its series of Summer Celebration weekends through Sept. 27, 2020. Local merchants will set out their wares in the historic downtown and railroad district for a fall sidewalk sale (Sept. 11-13), a great way to show your love to local businesses. Another week of the summer celebration (Sept. 18-20) includes a fall harvest festival, designed to showcase the region’s agricultural bounty with tours. Dine at some of the city’s best restaurants, like Peerless Restaurant & Bar global cuisine, Brickroom for modern-American fare and cocktails, and Smithfields steakhouse. Many Ashland restaurants have expanded their patios for socially distant outdoor dining, which will last as long as the weather allows. Ashland is a launching point for exploring Southern Oregon’s esteemed Rogue Valley Wine Country — from its convenient urban tasting rooms to the boutique, family-owned vineyards along the Bear Creek, Applegate Valley and Upper Rogue wine trails. In and around Ashland, Grizzly Peak Winery, Dana Campbell Vineyards, Belle Fiore, Platt Anderson Cellars and Weisinger Family Winery offer everything from cozy fire pits and bocce courts to paired bites, award-winning vintages and stellar views.

Get Your Art On

While Oregon Shakespeare Festival shows are canceled for 2020, visitors may get a taste of the world-class entertainment with a series of “Green Shows on the Go” through September, if social-distancing requirements allow. The festival — among the oldest and largest professional nonprofit theaters in the nation — would take its beloved free Green Show on the road to communities around Ashland with mesmerizing live song, dance and storytelling performances from all genres and cultures. The tradition dates back to 1960. Check the festival’s website and Facebook page for updates. In the meantime, locals can take a self-guided tour of the city’s vibrant public art and the historic sites and features of Lithia Park, including the large Rose Garden and Japanese Garden.

Play Outside

Ashland is a recreation paradise year-round, but fall is especially enchanting, with autumn colors on full display along the nature trails at Lithia Park, in the center of town. Just outside of the city, water enthusiasts may head to the Rogue or Upper Klamath rivers for a whitewater rafting or paddling trip — book a private guided tour for the best experience. Or head to any of the numerous mountain lakes to swim, fish or have a picnic. Cyclists may hit the trail along the Cascade Siskiyou Scenic Bikeway, a 55-mile loop that climbs up to 5,000 feet in elevation, or explore the off-road trail systems at the Ashland Watershed or Oredson-Todd Woods & Siskiyou Mountain Park. Hikers in search of a worthy day trip will have an epic trek at the 3-mile out-and-back Grizzly Peak Trail, 12 miles east of town, for outstanding views of the Cascade mountains and beyond. There’s plenty for families, too. Rogue Valley ZipLine Adventure in Central Point, 17 miles north, takes families (including children ages 8 or older) on a thrilling tour through the tree canopy with views of Crater Lake Rim, Mt. McLoughlin, Table Rocks and other landmarks. Reservations may be made for groups up to 10 people, with temperatures checked before the tour. Groups are required to stay at least 6 feet apart and wear face coverings for the shuttle ride to the park.  

About The

Jen Anderson
Jen Anderson is a longtime journalist and travel writer/editor who is now Travel Oregon’s Content & Community Manager, helping to align content for visitors via social media, print and web. She’s called Oregon home for 25 years and loves finding the latest places to eat, drink and play around the state with her husband and two boys. Brewpubs, beaches and bike trails top the list.

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