Scenic Road Trip from Woodstock, MD to Jackson Hole, WY: A 4-Day Adventure

Day 1: Woodstock to Pittsburgh

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

8:00am

Breakfast at Blue Moon Cafe

Start your journey with a hearty breakfast at the Blue Moon Cafe in Woodstock, known for its delicious coffee and fresh pastries.
USD15, 1h

9:30am

Drive to Pittsburgh via Scenic US-40

Take the historic National Road (US-40 West) for a scenic drive through charming small towns and beautiful countryside views leading towards Pittsburgh.
USD0, 6h0m

4:00pm

Pittsburgh Riverwalk

Relax and stretch your legs along the scenic Pittsburgh Riverwalk, offering beautiful views of the Allegheny and Ohio Rivers.
USD0, 1h

6:00pm

Dinner at Primanti Bros.

Enjoy iconic Pittsburgh sandwiches stuffed with coleslaw and fries at Primanti Bros., a must-try local favorite.
USD20, 1h
View Hotels

Day 2: Pittsburgh to Chicago

Pittsburgh, PA to Chicago, IL on June 8, 2025

7:30am

Breakfast at Pamela's Diner

Fuel up with classic diner breakfast pancakes and coffee at Pamela's Diner in Pittsburgh before hitting the road.
USD15, 1h

9:00am

Drive to Chicago via I-80 W

Drive west with a planned stop or two along the Ohio and Mississippi Rivers, enjoy scenic river views and small towns en route to Chicago.
USD0, 8h30m

6:00pm

Dinner at Giordano's Deep Dish

Indulge in Chicago’s famous deep-dish pizza at Giordano's, perfect for fueling up after a long drive.
USD25, 1h30m
View Hotels

Day 3: Chicago to Rapid City

Chicago, IL to Rapid City, SD on June 9, 2025

7:00am

Breakfast at Wildberry Pancakes and Cafe

Enjoy breakfast near Millennium Park at Wildberry Pancakes and Cafe, known for waffles and fresh fruit toppings.
USD20, 1h

8:30am

Drive to Rapid City via I-90 W

Take I-90 West for a long scenic drive through the prairies and plains of the Midwest, with optional stops at Sioux Falls or Badlands National Park for breathtaking views.
USD0, 11h30m

6:00pm

Dinner at The Corn Exchange

Comfort food with a western twist awaits at The Corn Exchange in Rapid City, perfect for a relaxing meal.
USD30, 1h
View Hotels

Day 4: Rapid City to Jackson Hole

Rapid City, SD to Jackson Hole, WY on June 10, 2025

7:00am

Breakfast at Firehouse Brewing Co.

Enjoy breakfast classics at Firehouse Brewing Co. in Rapid City before heading into the scenic mountainous region.
USD20, 1h

8:30am

Drive through Badlands National Park and Black Hills to Jackson Hole

Travel west through the striking Badlands rock formations, then the forested Black Hills en route to the stunning Grand Teton region near Jackson Hole.
USD30 park entrance fee, 6h

3:00pm

Explore Jackson Hole Town Square

Stroll through the iconic elk antler arches and boutique shops in Jackson Hole’s charming town square.
USD0, 1h

6:00pm

Dinner at Snake River Grill

Dine at the upscale Snake River Grill featuring local game and fresh regional ingredients, an excellent way to end your scenic road trip.
USD50, 1h30m
View Hotels