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Scenic 5-Day Road Trip from Woodstock, MD to Jackson Hole, WY

Viewed by 119 travelers

Day 1: Appalachian Mountain Scenic Drive

Woodstock, MD to Harrisburg, PA on June 7, 2025

8:00am

Breakfast at Woodstock Cafe

Start your trip with a tasty breakfast featuring fresh, local ingredients at Woodstock Cafe, open from 7:00am to 3:00pm.
USD15, 1h0m

9:00am

Drive via Appalachian Trail Scenic Byway

Take the scenic route along the Appalachian Trail Byway through Pennsylvania, enjoying lush mountain views and occasional hiking opportunities along the route.
Free, 4h30m

1:30pm

Lunch at Appalachian Brewing Company, Harrisburg

Enjoy craft brews with farm-to-table dishes at this popular brewery open from 11:00am to 10:00pm, offering scenic river views.
USD20, 1h0m

2:30pm

Explore Harrisburg Riverfront Park

Stretch your legs in this beautiful urban park along the Susquehanna River featuring walking trails and scenic overlooks.
Free, 1h0m

4:00pm

Drive to overnight lodging in Harrisburg

Check into a comfortable hotel in Harrisburg for a restful evening.
USD100, N/A

7:00pm

Dinner at The Millworks

Dine on creative American cuisine in a rustic industrial setting at The Millworks, open until 9:00pm.
USD30, 1h30m
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Day 2: Ohio Countryside & River Drive

Harrisburg, PA to Columbus, OH on June 8, 2025

7:30am

Breakfast at Little Amps Coffee Roasters

Savor freshly brewed coffee and pastries at this local favorite, open from 7:00am.
USD10, 1h0m

8:30am

Drive through Amish Country, Holmes County, OH

Experience the beautiful farmlands and quaint towns of Amish Country, stopping to visit markets or handcrafted goods stores open during daylight hours.
Free to explore, 3h0m

11:30am

Lunch at Blue Gate Restaurant, Shipshewana

Enjoy hearty Amish-style meals in a cozy setting, open from 7:00am - 7:00pm.
USD18, 1h0m

12:30pm

Drive scenic Ohio River stretch toward Columbus

Continue your journey west through Ohio’s rolling hills and along river vistas toward Columbus.
Free, 3h30m

4:00pm

Check-in and rest at hotel in Columbus

Relax after a scenic drive or explore downtown Columbus in the evening.
USD110, N/A

7:00pm

Dinner at The Pearl

Indulge in upscale coastal cuisine featuring fresh seafood at this popular spot open until 10:00pm.
USD35, 1h30m
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Day 3: Illinois River Views & Prairie Land

Columbus, OH to Davenport, IA on June 9, 2025

7:30am

Breakfast at Stauf’s Coffee Roasters

Enjoy a robust coffee and light breakfast in Columbus’s trendy East Side, open from 7:00am.
USD12, 1h0m

8:30am

Drive through Indiana farmland and stops in Springfield, IL

Pass through vast farmland and stop in Springfield for a quick visit to Abraham Lincoln sites open 9:00am to 5:00pm.
USD15, 4h0m

12:30pm

Lunch at Cozy Dog Drive In, Springfield

Try the original corn dog at this nostalgic eatery open until 7:00pm.
USD10, 1h0m

1:30pm

Continue drive to Davenport via Great River Road

Enjoy drives along the Mississippi River with beautiful bluffs and river views.
Free, 3h30m

5:00pm

Check-in hotel in Davenport, IA

Evening to relax or enjoy riverfront walks.
USD90, N/A

7:00pm

Dinner at Machine Shed Restaurant

Savor hearty Midwestern fare in a unique barn setting, open until 9:00pm.
USD25, 1h30m
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Day 4: Nebraska Plains & Badlands

Davenport, IA to Alliance, NE on June 10, 2025

7:00am

Breakfast at Morningstar Coffee and Cafe

Enjoy breakfast and a strong coffee in Davenport's historic district, open at 6:30am.
USD15, 1h0m

8:00am

Drive through Nebraska, visit Scotts Bluff National Monument

Pause at this natural landmark to enjoy amazing vistas and hiking; visitor center open 8:00am–6:00pm.
USD7 per vehicle, 2h0m

11:00am

Drive to Alliance, NE with scenic plains views

Continue westward over open plains toward your evening stop in Alliance.
Free, 2h30m

1:30pm

Lunch at Range Café, Alliance

Dine on regional specialties at this cozy local favorite open from 11:00am to 3:00pm.
USD18, 1h0m

2:30pm

Explore local art and history at the Knight Museum & Sandhills Center

Learn about the natural and cultural history of the region, open 10:00am - 5:00pm.
USD5, 1h0m

4:00pm

Relax at hotel in Alliance

Prepare for the final leg of your scenic trip tomorrow.
USD90, N/A

7:00pm

Dinner at The Anchor West Steakhouse

Enjoy quality steak and local dishes in a rustic setting, open until 9:00pm.
USD35, 1h30m
Find Hotels in Davenport

Day 5: Wyoming Mountains Arrival

Alliance, NE to Jackson Hole, WY on June 11, 2025

7:00am

Breakfast at hotel or local cafe

Get a hearty meal to start your last day of the scenic drive, most cafes open 7:00am.
USD15, 1h0m

8:00am

Drive through the scenic Nebraska Sandhills to Wyoming

Pass through impressive sand dunes and rolling hills as you enter Wyoming, watching for wildlife in natural settings.
Free, 4h0m

12:00pm

Lunch stop in Casper, WY - The Fort Restaurant

Experience authentic Old West dining in Casper, open from 11:00am to 9:00pm.
USD25, 1h0m

1:00pm

Final drive to Jackson Hole

Enjoy magnificent mountain views as you approach the scenic valley known for its wildlife and outdoor activities.
Free, 3h0m

4:00pm

Arrival and check-in at Jackson Hole lodging

Settle into your hotel or lodge and take in stunning Tetons panoramic views.
USD150, N/A

7:00pm

Dinner at Snake River Grill

Enjoy a refined dining experience with local game and fresh ingredients, open until 10:00pm.
USD40, 1h30m
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