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Scenic Road Trip from Menomonie, WI to Barnard, VT with Food and Sightseeing Stops

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Day 1: Departure and Chicago stop

Menomonie, WI to Chicago, IL on May 17, 2025

7:30am

Breakfast at The Workshop Cafe, Menomonie

Enjoy a delicious start with hearty breakfast options made from fresh local ingredients to fuel your journey.
USD15, 1h

8:30am

Drive from Menomonie to Chicago

Embark on approximately a 5.5-hour drive of about 350 miles heading southeast towards Chicago, IL.
USD0, 5h30m

2:00pm

Lunch at Lou Malnati’s Pizzeria, Chicago

Stop for a famous deep-dish Chicago-style pizza lunch at Lou Malnati’s, open daily 11am-11pm.
USD25, 1h

3:30pm

Millennium Park Visit

Explore Millennium Park and see the iconic Cloud Gate sculpture, walking around and enjoying city views. Open all day.
USD0, 1h

5:00pm

Check-in to Chicago hotel

Rest up at your hotel in Chicago for the night to prepare for the next day’s drive.
USD150, Overnight

7:00pm

Dinner at Girl & The Goat

Enjoy innovative small plates at one of Chicago’s most famous restaurants, open 5pm-10pm.
USD50, 1.5h
Find Hotels in Menomonie

Day 2: Midway driving and sightseeing

Chicago, IL to Cleveland, OH on May 18, 2025

8:00am

Breakfast at Yolk

Begin your day with creative and tasty breakfast options at this popular spot, open 7am-3pm.
USD20, 1h

9:00am

Drive Chicago to Cleveland

Travel approximately 340 miles east toward Cleveland, OH on a 6-hour drive.
USD0, 6h

3:00pm

Visit Rock & Roll Hall of Fame

Explore this iconic museum open daily 10am-5:30pm to dive into music history.
USD30, 1.5h

5:00pm

Check-in Cleveland Hotel

Rest at your hotel in Cleveland and recharge for the next driving leg.
USD130, Overnight

7:00pm

Dinner at Slyman’s Tavern

Try Cleveland’s famous corned beef sandwich at this local pub open till 10pm.
USD20, 1h
Find Hotels in Chicago

Day 3: Scenic New York State route

Cleveland, OH to Albany, NY on May 19, 2025

7:30am

Breakfast at Blue Door Cafe & Bakery

Grab a fresh and tasty breakfast before hitting the road, open 7am-2pm.
USD15, 1h

8:30am

Drive Cleveland to Albany

Take the 5.5-hour drive, approximately 350 miles east, entering New York State with scenic views.
USD0, 5h30m

2:00pm

Lunch at The Hollow Bar + Kitchen, Albany

Enjoy modern American cuisine in a lively downtown spot, open 11:30am-10pm.
USD25, 1h

3:30pm

Walk along the Albany Waterfront

Stroll the scenic Hudson River waterfront to stretch your legs before resting.
USD0, 1h

5:00pm

Check-in Albany Hotel

Rest up at your hotel in Albany tonight.
USD140, Overnight

7:00pm

Dinner at Yono’s Restaurant

Experience award-winning fine dining with an adventurous menu, open 5:30pm-9pm.
USD60, 1.5h
Find Hotels in Cleveland

Day 4: Final leg to Barnard, VT

Albany, NY to Barnard, VT on May 20, 2025

8:00am

Breakfast at Iron Gate Cafe, Albany

Enjoy a cozy breakfast in a historic setting, open daily 8am-2pm.
USD15, 1h

9:00am

Drive Albany to Barnard

Complete the last 90-mile 2-hour drive heading northeast across the scenic Vermont countryside.
USD0, 2h

11:00am

Arrival in Barnard, VT

Arrive at your destination and explore the charming village, enjoying rural Vermont atmosphere.
USD0, Flexible

12:30pm

Lunch at Barnard General Store

Experience local homemade sandwiches and baked goods in this well-loved village spot.
USD15, 1h

2:00pm

Outdoor leisure time

Enjoy hiking or kayaking in Barnard State Park or nearby Silver Lake if weather permits.
USD0-10, Flexible

7:00pm

Dinner at The Richardson Farmstead Restaurant

Dine farm-to-table style with locally sourced Vermont fare in a warm rustic setting.
USD40, 1.5h
Find Hotels in Albany
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