
Road Trip to the
La Crosse Region
from Milwaukee
The La Crosse Region makes for the perfect fall weekend getaway, and you could be here by lunch! Only a 3-hour drive away, escape and explore the ancient topography, charming history, and elevated adventure of the Driftless!
A Long-Weekend Itinerary
in the La Crosse Region
Day 1: An Afternoon of Exploring
Afternoon: BBQ Lunch & River Views
Hop off the highway in West Salem for lunch at Big Boar Barbecue on your way into the Driftless Region. After lunch, head to Onalaska and the Great River Landing, the trailhead for the Great River State Trail for a scenic stroll through fall colors along the Mississippi River Valley. After you’ve explored through state trails, venture over to the Upper Mississippi River National Wildlife & Fish Refuge for more beautiful trails and views of Lake Onalaska.
Big Boar Barbecue
Great River Landing & Great River State Trail
Upper Mississippi River National Wildlife & Fish Refuge La Crosse District Visitor Center
Evening: Explore Downtown La Crosse
After spending an afternoon enjoying the Mississippi River views, swing by Starlite Lounge for a classic cocktail, then enjoy dinner at Pizzeria Dolorosa in downtown La Crosse. Stop by the Pearl for an after dinner ice cream treat before heading to your hotel to check-in, relax, and plan your route for tomorrow.
The Starlite Lounge
Pizzeria Dolorosa
The Pearl Ice Cream Parlor
Lodging
Day 2: Hiking, Paddling, & Fine Dining in
the La Crosse Region
Morning: Hike the Bluffs
A visit to the La Crosse Region in the fall would be amiss without enjoying the colorful view from the bluffs. Stop for breakfast at JavaVino before exploring a multitude of hiking trail options. With many interconnected trails and a range of difficulty, there is something for everyone.
JavaVino
Grandad Bluff
Gateway Trails
Lower Hixon Trails
Afternoon: Fall Fun in the La Crosse Region
After a morning of hiking, head north to Onalaska for a waterfront lunch at Red Pines. From there, stop by Ferguson’s Orchard for an afternoon of apple picking and a pumpkin patch.
Red Pines Bar & Grill
Ferguson’s Orchards
Evening: Drinks & Dinner
After a day exploring outdoors, unwind with drinks and dinner at two local favorites in downtown La Crosse. Stop for cocktails at The Hatchery, a former fish hatchery turned boutique hotel, then enjoy dinner at Lovechild, a modern restaurant serving locally sourced, seasonal cuisines.
The Hatchery
Lovechild
Day 3: Coffee & Biking in La Crosse
Grab breakfast and coffee at Jules Coffee House, then enjoy a leisurely bike ride in the La Crosse Region to soak up the fall colors before you head home.
Jules Coffee House
Drift Cycle Bike Share at Riverside Park
Explore More Outdoor Itineraries
Warm-Up & Play in Fresh Winter Air!
For the Avid Adventurer
Scenic Sights & Hidden Gems of the Driftless Region

Dive into Our Visitors Guide
Check out La Crosse’s Visitors Guide to explore the best attractions, dining, and events in the area!