5-Day Winter Itinerary for Outdoor Enthusiasts in Deadwood, SD

Deadwood offers a winter wonderland perfect for outdoor enthusiasts. From skiing and snowshoeing to snowmobiling and hiking, this charming town has plenty of activities to keep you busy. Here’s a detailed 5-day itinerary to help you make the most of your winter adventure!


Day 1: Arrival & Exploring Historic Deadwood

Morning: Arrival in Deadwood

  • Check-in to your Deadwood Connections rental: Choose from a selection of cozy vacation rentals that offer comfort and easy access to local attractions.
  • What to Bring: Warm clothing, snow boots, gloves, hats, and a camera.

Afternoon: Historic Deadwood Tour

  • Activity: Take a leisurely stroll through the historic downtown area. Visit the Adams Museum to immerse yourself in Deadwood’s rich history.
  • Food Recommendation: Enjoy lunch at The Deadwood Social Club, where you can savor hearty sandwiches and local beers.

Evening: Relax & Enjoy Dinner

  • Activity: Experience the lively atmosphere at The Saloon No. 10, known for its live music and historic charm.
  • Dinner Recommendation: Indulge in a delicious Bison Steak at Deadwood Legends Steakhouse a local favorite for fine dining.

Local Tip: Be sure to pick up a winter guide map at the visitor center to find the best spots in town!

Day 2: Skiing at Terry Peak

Morning: Head to Terry Peak

  • What to Bring: Ski or snowboard gear (rentals available at the resort), warm layers, and goggles.
  • Activity: Drive to Terry Peak Ski Area (approx. 15 miles from Deadwood) for an exciting day on the slopes.

Afternoon: Hit the Slopes

  • Activity: Enjoy skiing or snowboarding on the resort’s various trails suitable for all skill levels.
  • Food Recommendation: Grab a quick lunch at the Stewart Lodge for warm drinks and hearty options.

Evening: Après-Ski

  • Activity: Unwind after your day on the slopes. Consider indulging in a local spa treatment to relax those muscles!
  • Dinner Recommendation: Visit The Lodge at Deadwood for a cozy dining experience featuring comfort food.

Local Tip: If you plan to ski again, consider purchasing a multi-day ski pass for better value.

Day 3: Snowshoeing & Sledding

Morning: Snowshoeing at Bear Butte State Park

  • What to Bring: Snowshoes (available for rent in Deadwood), warm clothing, water, and snacks.
  • Activity: Venture to Bear Butte State Park (about 20 minutes from Deadwood) for some picturesque snowshoeing.

Afternoon: Sledding Fun

  • Activity: Head to Dumont Lake for a fun-filled afternoon of sledding and winter games. Bring your own sled or rent one nearby.
  • Food Recommendation: For lunch, try Jacobs Brewhouse Restaurant for homestyle cooking & smoked brisket, plus a grocer with health-conscious fare.

Evening: Ghost Tour

  • Activity: Discover Deadwood’s haunted history with a guided ghost tour.
  • Dinner Recommendation: Enjoy a casual meal at Mavericks Steak & Cocktails, featuring a variety of comfort food options.

Local Tip: Don’t forget your camera! The views from Bear Butte are stunning, especially with a blanket of snow.

Day 4: Snowmobiling Adventure

Morning: Snowmobiling at Black Hills

  • What to Bring: Warm layers, gloves, and a helmet (rentals available at local shops).
  • Activity: Rent a snowmobile and explore the scenic trails of the Black Hills National Forest, accessible just a short drive from Deadwood.

Afternoon: Scenic Rides and Lunch

  • Activity: Take a break at Iron Creek Lake for lunch. Pack a hearty meal from one of Deadwood’s local eateries or grab sandwiches from a deli.
  • Food Recommendation: Stop by Earl of Sandwich for quick and delicious options.

Evening: Relaxation and Dinner

  • Activity: After an adventurous day, unwind with a casual evening stroll around Deadwood.
  • Dinner Recommendation: Dine at Buffalo Bodega Saloon & Steakhouse, known for yummy lunch and dinner options served in an old west atmosphere.  Great steaks, ribs, chicken, sandwiches, prime rib.  Kids menu too!

Local Tip: Always check trail conditions and weather forecasts before heading out for safety.

Day 5: Hiking & Departure

Morning: Hike in Spearfish Canyon

  • What to Bring: Hiking boots, warm layers, and water.
  • Activity: Drive to Spearfish Canyon (about 20 minutes from Deadwood) and hike the Roughlock Falls trail for stunning winter scenery.

Afternoon: Scenic Drive and Lunch

  • Activity: Enjoy the breathtaking views of the canyon and stop at Bridal Veil Falls for a short hike.
  • Food Recommendation: Have a farewell lunch at The Spearfish Canyon Lodge, which offers hearty meals with stunning views.

Evening: Departure

  • What to Do: Before you leave, explore any last-minute shops in Deadwood for souvenirs and gifts.
  • Local Tip: If time allows, visit The Days of ’76 Museum to learn more about Deadwood’s history and the famous rodeo.

Final Tips for Your Trip

  • Weather: Always check the weather forecast before venturing out, as winter conditions can change quickly.
  • Gear Rentals: Most outdoor gear can be rented in town through local shops affiliated with Deadwood Connections.
  • Stay Hydrated and Energized: Pack snacks and water, especially during outdoor activities, to keep your energy up.

With this itinerary, outdoor enthusiasts can enjoy an unforgettable winter experience in Deadwood with the comfort of Deadwood Connections! Happy travels!