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Outdoor Happenings: August-November 2023

The top outdoor races, festivals, events, and experiences in the Blue Ridge and Beyond. Check out some of our top picks here and online at

August 2023

High Knob Outdoor Fest

August 14-19

Norton, VA

Get Outside in Norton at the High Knob Outdoor Fest! This weeklong celebration of the High Knob Region’s outdoor recreation opportunities features 10+ outdoor trips and educational events and a downtown festival offering live music, food trucks, a beer garden, outdoor vendors/demos, and more.

Midnight Flight

August 25

Anderson, SC

Midnight Flight has been a tradition in the Anderson Community for 46 years. Over 1000 runners participated last year. The road-race is a certified Grand-Prix race and the largest night-time race in South Carolina. The 1 mile will begin at 8:15 p.m., and the 5K at 9 p.m.

Ashland Half Marathon

August 26

Ashland, VA

If you’ve never been to Ashland, Virginia look no further than the Ashland Half Marathon to find yourself soaking in every ounce of the colorful town! Escape to small-town Virginia and run 13.1 miles along rolling hills, picturesque fields, and maybe even spot a train or two.

Sky Meadows State Park 40th Anniversary Celebration

August 26

Delaplane, VA

Join Sky Meadows State Park for its special 40th anniversary celebration. The event features live music, local wine and beer vendors, food trucks, wagon rides, Mount Bleak Open House, conservation programs, historic demonstrations and more. Admission is free.

Front Porch Fest 14

August 31 – September 3

Stuart, VA

Held at the foot of the Blue Ridge, Front Porch Fest was born from the idea that life is art, and music is the soul. Featuring a high caliber of artists, this small family-friendly festival is a “don’t miss” in the region and a great event for first time festival goers.

September 2023

Bertha Cave Explorers New River Trail State Park

September 2

Max Meadows, VA

Come learn what makes cave ecosystems so delicate and special. In this adventure, you will have the opportunity to see unique formations and animals that only exist in caves. Please wear clothes that can get dirty and non-slip close-toed shoes. Registration is required, space is limited. $20.

Let’s Go Kayaking at Shenandoah River State Park

September 2

Bentonville, VA

Paddling a kayak gives you a new perspective of the world. This 8 hour class will cover the basics of paddling skills including; how to select and fit a PFD, different types of kayaks, planning and safety, and proper paddling strokes. Advanced registration required. $15.

Bobby Weir & Wolf Bros featuring The Wolfpack

September 13

Charlottesville, VA

Bobby Weir & Wolf Bros formed in 2018 by Weir along with Don Was and Jay Lane, performing the expansive catalogue of Grateful Dead, Bobby’s solo albums and more. Jeff Chimenti joined in 2020, around the same time they started featuring The Wolfpack, a string and brass quintet.

The Infamous Weekend

September 15-16

Martinsville, VA

This inaugural family-friendly event features 2 days and nights of amazing music from festival hosts, The Infamous Stringdusters plus a supporting lineup curated by the band itself. Enjoy on-site camping, outdoor activities, food, drink, arts, and kids’ activities at the idyllic Pop’s Farm in the rolling foothills of Martinsville, Va.

Powhatan State Park Pawpaw Festival

September 16

Powhatan, VA

Check out Central Virginia’s most exciting new event, the Inaugural Pawpaw Festival. Experience the beauty of these trees and learn more about the nation’s largest native fruit. The event will feature acoustic music performances, ranger-led programs, crafts and wildlife. Admission is $5; children 12 and under free.

World Chicken Festival

September 21 – 24

London, KY

Top-notch free entertainment, thrilling amusement rides, outrageous contests, quality craft & food vendors and the World’s Largest Skillet that cooks up mouth-watering fried chicken! Check this off your bucket list and join us for a fun and fabulous festival! 

Kiptopeke State Park Outdoor Exploration Day

September 23

Kiptopeke, VA

Come celebrate National Public Lands Day and the great Eastern Shore of Virginia at our Outdoor Exploration Day. Through education, hands-on demonstrations and outdoor recreation, visitors will further their appreciation of the Eastern Shore and Chesapeake Bay.

Peach Kid’s Triathlon Championship Presented by Children’s Healthcare of Atlanta

September 24

Alpharetta, GA

A high-quality youth triathlon experience for the entire family that is focused on fitness, fun, and safety. All finishers will receive commemorative medals.

Gov’t Mule with G. Love & Special Sauce

September 29

Charlottesville, VA

Gov’t Mule, known for their bluesy, hard rock riffing, songwriting, and virtuosic improvisation are joined by G. Love & Special Sauce, creators of their own genre, “The Hip-Hop Blues” – a laid back, rootsy sound, that encompasses Delta blues, hip hop, rock & roll soul and funk.

October 2023

Alley Fest

October 6 – 7

Paintsville, KY

The Alley Fest is the best musical entertainment that Eastern Kentucky has to offer. Celebrating the area’s rich musical heritage with some of the nation’s hottest acts. This two day event is sure to highlight Paintsville, KY.

Kentucky Apple Festival

October 6 – 7

Paintsville, KY

The Kentucky Apple Festival has been a celebration of community, fall harvest, and local nonprofits since it’s beginning in 1973. Our event offers craft vendors, music concerts, carnival rides, and a parade.

Oktobrewfest 2023

October 7, 5-10PM

Historic Main St, Tazewell, VA 

An evening of music, craft beer and cider, wine and food, featuring live performances from Mackenzie Phipps and Steele Cookin Band, as well as a Beer Stein competition–and an After Brewfest Party from 10:00pm-Midnight at Back of the Dragon!  Get the party started early at the Friday Night Kickoff on October 6th with dinner and drink specials at local Tazewell County restaurants.

LEAF Global Arts Festival

October 19 – 22

Black Mountain, NC

LEAF Festival offers opportunities to connect to the world and each other at the scenic Lake Eden. Live music, dance, and performance arts are offered alongside camp and lake outdoor adventures, healing arts workshops and practitioners, poetry slam in the world, kids adventures and workshops, mountain drum circle, and more!

NC Liver Mush Festival – Mush, Music & Mutts

October 21

Washington Street, Uptown Shelby, NC

Recognized in regional and national media, this festival celebrates the unique delicacy known as liver mush. Festival highlights include a liver mush eating contest, recipe contest and cook-off, live music, and more than 80 craft, food, and beverage vendors. Free to attend, pets welcome, and fun for the whole family!

Bluegrass Mountain Cup

October 27 – 29

Prestonsburg, KY

Prestonsburg is the Mountain Biking Capital of Kentucky, and for good reason. Experienced riders find thrill alongside magic views on Sugarcamp Mountain. Prestonsburg is happy to host the KY Mountain Bike Summit on 10/27 before once again welcoming the Bluegrass Mountain Cup on October 28-29 for XC and Enduro races.

November 2023

Alpharetta Women’s Half Marathon and 5K Race Presented by Altra

November 5

Alpharetta, GA

Pack your running shoes and join us for the Alpharetta Women’s Half Marathon & 5k presented by Altra. After crossing the finish line, participants are invited to celebrate with a post-race party.

Allianz Partners Richmond Marathon

November 11

Richmond, VA

Whether you take part in the marathon, CarMax Richmond Half Marathon, or VCU Health Richmond 8k, Richmond provides phenomenal course support, great fall scenery, and awesome finisher swag. Don’t miss the 46th running of America’s Friendliest Marathon!

The Bay Bridge Run/Walk

November 13

Annapolis, MD

Your only chance to run/walk across the majestic Chesapeake Bay Bridge which is typically closed to pedestrians.  You can expect a fun, well managed event open to runners and walkers alike.  The 10K course will traverse the eastbound span of the bridge from Anne Arundel County to Kent Island.

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