Scenic Driving Itinerary from Urbana, MD to Hamilton, OH via Kentucky with Comfortable Daily Drives

Day 1: Urbana to Charleston

Urbana, MD to Charleston, WV on June 12, 2025

8:00am

Breakfast at The Urbana Cafe

Start your day with hearty American breakfast options in a cozy local spot to fuel up for the scenic drive ahead.
USD15, 1h

9:30am

Drive from Urbana to Charleston

Begin your approximately 4.5-hour scenic drive traveling through picturesque rural Maryland, Pennsylvania, Ohio, and West Virginia landscapes. Enjoy stops at overlooks and small towns as you go.
Free, 4h30m

2:30pm

Lunch at Bluegrass Kitchen, Charleston, WV

Dine on farm-to-table Appalachian cuisine featuring fresh local ingredients, offering a true taste of West Virginia.
USD20, 1h

4:00pm

Visit Haddad Riverfront Park

Enjoy a relaxing walk along the Kanawha River with beautiful views, perfect after a day of driving.
Free, 1h

6:30pm

Dinner at Black Sheep Burrito & Brews

Casual dining with creative burritos and local craft beers, perfect for a laid-back evening meal.
USD18, 1h
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Day 2: Charleston to Lexington

Charleston, WV to Lexington, KY on June 13, 2025

8:00am

Breakfast at Sunrise Carwash & Coffee Bar

Grab coffee and tasty morning snacks in a quirky local spot before hitting the road.
USD10, 45m

9:00am

Drive from Charleston to Lexington

Travel about 3.5 hours through scenic Appalachian foothills and into Kentucky’s horse country, enjoying rolling hills and nature vistas.
Free, 3h30m

12:30pm

Lunch at Wallace Station Deli & Bakery, Versailles, KY

Stop in a charming town just outside Lexington for sandwiches and fresh baked pastries fresh from the bakery.
USD15, 1h

2:00pm

Visit Keeneland Race Course

Explore the historic horse racing track and museum, an important site in Lexington’s equestrian culture. Open daily 10am-5pm.
USD10, 1h30m

4:00pm

Drive into downtown Lexington

Check into your accommodation and take a brief rest before dinner.
Varies, 30m

6:30pm

Dinner at Coles 735 Main

Savor upscale southern cuisine in a relaxed atmosphere downtown, known for fresh local ingredients and elegant dishes.
USD40, 1h30m
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Day 3: Lexington to Hamilton

Lexington, KY to Hamilton, OH on June 14, 2025

8:00am

Breakfast at Katherine’s

Enjoy a locally beloved breakfast spot featuring homemade baked goods and quality coffee before heading out.
USD12, 1h

9:30am

Drive from Lexington to Hamilton

Finish the approximately 3.5-hour drive through northern Kentucky into Ohio, passing scenic river valleys and rolling countryside.
Free, 3h30m

1:00pm

Lunch at The Golden Lamb, Lebanon, OH

Stop for lunch at Ohio’s oldest inn and restaurant offering classic American fare steeped in history.
USD20, 1h

3:00pm

Arrive in Hamilton, OH and Visit Fitton Center for Creative Arts

Explore local art exhibits and community events at this downtown Hamilton cultural center. Open 12pm-5pm Tuesdays-Saturdays.
Free, 1h

5:00pm

Dinner at The Liberty Wine Bar

Wrap up your trip in style with wine and small plates in a cozy, intimate setting.
USD35, 1h30m
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