Fair in the Square returns to Outlaw Square in historic Deadwood September 11–12, 2026, bringing together local artisans, makers, and visitors for a celebration of creativity and craftsmanship. This open-air juried craft fair showcases unique handmade goods, one-of-a-kind artwork, and specialty items from talented vendors in a welcoming downtown setting. Whether you’re searching for a... Read more »

Deadwood Jam returns to historic Deadwood September 18–19, 2026, bringing two days of live music, community, and unforgettable entertainment to the heart of the Black Hills. Celebrating its 36th annual festival, Deadwood Jam is one of the region’s premier outdoor music events, featuring a diverse lineup of talented performers, local artists, and an atmosphere that... Read more »

The Mickelson Trail Trek returns to the Black Hills September 18–20, 2026, inviting cyclists to experience one of South Dakota’s most scenic and historic trails. This annual three-day ride takes participants along the George S. Mickelson Trail, a 100-plus-mile route that winds through breathtaking landscapes, historic mining towns, tunnels, and the heart of the Black... Read more »

Oktoberfest in Deadwood returns to historic Deadwood October 2–3, 2026, bringing a taste of German tradition mixed with the Wild West charm that makes Deadwood unique. This annual celebration features live music, delicious food, local festivities, and crowd favorites like the famous Wiener Dog Races and Beer Barrel Games. From exploring downtown events to enjoying... Read more »

The Wild West Songwriters Festival returns to historic Deadwood October 15–17, 2026, bringing together talented songwriters, musicians, and music fans for a one-of-a-kind celebration of storytelling through song. Featuring writers behind some of country music’s biggest hits, the festival gives guests the opportunity to hear the stories behind the songs through intimate writer’s rounds, live... Read more »

Deadweird returns to historic Deadwood October 30–31, 2026, bringing a weekend of spooky fun, creative costumes, and Halloween excitement to the heart of the Black Hills. This annual celebration transforms Deadwood into a lively Halloween destination with themed parties, live entertainment, costume contests, and plenty of unforgettable moments throughout town. From the legendary Monster Ball... Read more »

Holiday Ho Ho Horseshoes returns to historic Deadwood November 13–December 30, 2026, bringing holiday cheer and a unique way to experience the magic of the season. This festive tradition invites visitors to purchase a special Deadwood holiday horseshoe ornament for a chance to win prizes from participating local businesses throughout town. Each horseshoe features a... Read more »

Kringle Crawl Weekend returns to Deadwood December 11–12, 2026, bringing holiday cheer, festive drinks, and a little extra fun to the historic streets of Deadwood. This merry holiday experience invites guests to enjoy seasonal cocktails, explore local establishments, and celebrate the season with friends during a unique holiday pub crawl. With festive decorations, holiday-inspired creations,... Read more »

New Year’s Eve in Historic Deadwood rings in the new year December 31, 2026, with an unforgettable celebration filled with excitement, entertainment, and the charm of the Wild West. Visitors can enjoy a festive atmosphere throughout downtown Deadwood, featuring special events, live entertainment, casino celebrations, and the iconic midnight ball drop at the Historic Franklin... Read more »