3 Days · Active Retirees
Driftless Area (Southwest), Wisconsin
Bluffs, Caves & River Light: 3 Days in the Driftless
4 stops
2 Days · Young Families
Driftless Area (Southwest), Wisconsin
Frost, Stone, and Underground Light: 2 Winter Days in the Driftless
4 stops
2 Days · Young Families
Hocking Hills, Ohio
Frost, Falls & Firelight: A Family Weekend in Hocking Hills
2 stops
3 Days · Young Families
North Shore (Gunflint/Grand Portage), Minnesota
Frost, Falls, and Fur Trade: 3 Winter Days on the North Shore
3 stops
3 Days · Active Retirees
Hocking Hills, Ohio
Stone Cathedrals in Winter Light: Hocking Hills at a Gentle Pace
3 stops
2 Days · Young Families
North Shore (Gunflint/Grand Portage), Minnesota
Frozen Falls & Lighthouse Light: A Family Winter Weekend on the North Shore
3 stops
3 Days · Young Families
Hocking Hills, Ohio
Waterfalls and Woolen Mittens: A Slow Winter Week in Hocking Hills
3 stops
2 Days · Couples
North Shore (Gunflint/Grand Portage), Minnesota
Frozen Light on Superior: Two Winter Days on the North Shore
4 stops
3 Days · Teen Families
Driftless Area (Southwest), Wisconsin
Bluffs, Ice, and Firelight: 3 Days in the Winter Driftless
4 stops
2 Days · Teen Families
Driftless Area (Southwest), Wisconsin
Bluffs, Crystals & River Silence: A Winter Weekend in the Driftless
3 stops
2 Days · Solo
North Shore (Gunflint/Grand Portage), Minnesota
Frozen Falls and Lonely Light: A Solo Winter Passage on the North Shore
3 stops
2 Days · Solo
Black Hills (non-Custer), South Dakota
Ice, Stone, and Silence: Two Days Alone in the Black Hills
4 stops
3 Days · Young Families
Driftless Area (Southwest), Wisconsin
Frost, Stone & Slow Valleys: 3 Days in the Driftless with Little Ones
4 stops
2 Days · Couples
Black Hills (non-Custer), South Dakota
Frozen Falls and Underground Starlight: 2 Days in the Black Hills
4 stops
2 Days · Active Retirees
Black Hills (non-Custer), South Dakota
Winter Hush: Two Days Beneath Stone and Ice in the Black Hills
4 stops
4 Days · Teen Families
Black Hills (non-Custer), South Dakota
Frozen Falls & Buried Starlight: 4 Winter Days in the Black Hills
7 stops
3 Days · Couples
Black Hills (non-Custer), South Dakota
Frost, Falls & Firelight: 3 Days in the Winter Black Hills
6 stops
3 Days · Couples
North Shore (Gunflint/Grand Portage), Minnesota
Ice, Falls & Firelight: A Winter Romance on the North Shore
4 stops
4 Days · Teen Families
Driftless Area (Southwest), Wisconsin
Bluffs, Caves & River Ice: 4 Days in the Driftless
6 stops
3 Days · Couples
Driftless Area (Southwest), Wisconsin
Bluffs, Caves & River Silence: 3 Winter Days in the Driftless
4 stops
4 Days · Teen Families
Hocking Hills, Ohio
Frost, Ferns & Stone: 4 Days Chasing Waterfalls in Hocking Hills
6 stops
4 Days · Teen Families
North Shore (Gunflint/Grand Portage), Minnesota
Ice, Falls & Firelight: Four Winter Days on the North Shore
6 stops
3 Days · Couples
Hocking Hills, Ohio
Frost, Falls & Firelight: A Winter Retreat in Hocking Hills
6 stops
The Midwest transforms into a winter wonderland during the colder months, offering travelers a chance to experience frozen waterfalls, snow-draped bluffs, and cozy retreats. This page features four distinct destinations—the Black Hills, North Shore, Driftless Area, and Hocking Hills—each with its own character and appeal. Visitors can choose from eight carefully curated itineraries ranging from three to four days, allowing flexible exploration of winter landscapes. Whether seeking romantic getaways, adventure through caves and forests, or peaceful winter solitude, these Midwest destinations deliver unforgettable seasonal experiences.
Frequently Asked Questions
How many itineraries are available for winter trips in these Midwest destinations?⌄
Eight itineraries are available across the four featured destinations, with options ranging from three to four days in length.
What destinations are covered on this winter trips page?⌄
The page features four Midwest destinations: the Black Hills, North Shore (Gunflint/Grand Portage), the Driftless Area, and Hocking Hills.
Are there itineraries for both short and extended winter trips?⌄
Yes. Travelers can choose from 3-day itineraries for shorter getaways or 4-day itineraries for more extended winter explorations.
What activities can visitors expect on these winter trips?⌄
Visitors can experience frozen and flowing waterfalls, caves, river ice, bluffs, ferns, and stone formations across the featured regions.
More Collections
Or see Winter Trips by state or browse weekend getaways in the Midwest.