21-Day Road Trip: Washington DC to Chicago and Back via Maryland, New York, Niagara Falls, and Ohio

Day 1: Arrival and Family Time

Washington DC, United States on July 16, 2025

8:00am

Arrival at Washington DC

Land at Washington Dulles International Airport and transfer to family home in Maryland for relaxation and re-acclimatisation.
USD0, 2h

10:00am

Breakfast at Founding Farmers

Enjoy a farm-to-table breakfast with hearty American classics just minutes from DC, open from 7am to 11am.
USD20, 1h

12:00pm

Family Visit in Maryland

Spend quality time with family, catching up and planning the days ahead.
USD0, 4h

6:00pm

Dinner at Uncle Julio’s in Bethesda, MD

Savour Mexican dishes in a lively setting, open until 10pm, perfect for a welcoming dinner with family.
USD30, 2h
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Day 2: Exploring Maryland

Maryland, United States on July 17, 2025

8:00am

Breakfast at Silver Diner

Classic American diner offering a wide variety of breakfast options, open from 6am.
USD15, 1h

9:30am

Visit Annapolis Historic District

Explore Maryland’s capital with charming streets, historic landmarks, and waterfront views, open to public at all times.
USD0, 3h

1:00pm

Lunch at Chick & Ruth’s Delly

Famous for their sandwiches and local charm, open from 10am to 8pm.
USD20, 1h

3:00pm

Relax at Sandy Point State Park

Enjoy scenic views of the Chesapeake Bay and a serene beach environment, open 8am to sunset.
USD7 entrance fee, 3h

7:00pm

Dinner at Woodberry Kitchen

Sample locally sourced Maryland cuisine in a rustic-chic setting, open until 10pm.
USD40, 2h
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Day 3: Family and Local Markets

Maryland, United States on July 18, 2025

8:30am

Breakfast at home with family

Enjoy a homemade breakfast with family for a cozy morning start.
USD0, 1h

10:00am

Visit Eastern Market, Baltimore

Explore this historic market for local crafts, fresh produce, and vibrant food stalls, open 7am-5pm.
USD0, 3h

1:30pm

Lunch at The Food Market

Contemporary American dishes in a casual setting, open 11am to 9pm.
USD25, 1.5h

3:30pm

Strolling Inner Harbor

Leisure walk along the waterfront with shops and museums, open all day.
USD0, 2h

7:00pm

Dinner at Thames Street Oyster House

Known for fresh seafood with a Maryland twist, open until 10pm.
USD40, 2h
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Day 4: Museum Day

Maryland, United States on July 19, 2025

8:00am

Breakfast at Dooby’s, Baltimore

Eclectic breakfast spot with vegan options, open from 7am.
USD18, 1h

9:30am

Visit the Walters Art Museum

Enjoy diverse collections from ancient to contemporary art, open 10am to 5pm, free admission.
USD0, 3h

1:00pm

Lunch at Miss Shirley’s Cafe

Southern-inspired dishes for a comforting lunch, open 7am to 3pm.
USD22, 1h

2:30pm

Explore Fort McHenry

Historic site that inspired the US national anthem, open 9am to 5pm.
USD15, 2h

6:30pm

Dinner at La Cuchara

Basque tapas with authentic flavours in a stylish locale, open till 10pm.
USD45, 2h
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Day 5: Nature and Relaxation

Maryland, United States on July 20, 2025

8:00am

Breakfast at The Food Market

Return to this favourite for fresh morning options before heading out.
USD18, 1h

9:30am

Day trip to Patapsco Valley State Park

Hiking, picnicking, and exploring nature trails in a vast forested area, park open dawn to dusk.
USD0, 5h

3:30pm

Late Lunch at One Lucky Duck

Organic and locally sourced light meals, open till 4pm, perfect after a nature walk.
USD18, 1h

7:00pm

Dinner at Family Home

Relax with a home-cooked meal with family after an active day.
USD0, 2h
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Day 6: Packing and Preparation

Maryland, United States on July 21, 2025

8:00am

Breakfast at Home

Casual breakfast with family before the journey ahead.
USD0, 1h

10:00am

Pack and prepare for road trip to New York

Get ready for departure with rest and organising belongings.
USD0, 3h

1:00pm

Lunch at Local Café

Grab sandwiches and coffee at a nearby café while finishing up preparations.
USD15, 1h

3:00pm

Depart for New York City

Start the drive north to NYC, approximately 4 hours drive.
USD50 fuel, 4h

7:30pm

Dinner at Carmine’s, NYC

Family-style Italian meals in Times Square, open till 11pm.
USD50, 2h
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Day 7: Explore New York City

New York City, United States on July 22, 2025

7:30am

Breakfast at Ess-a-Bagel

Famous NYC bagels with classic fillings, open from 6:30am.
USD15, 1h

9:00am

Visit Statue of Liberty & Ellis Island

Take a ferry and guided tour, ferries run from 8:30am to 5pm, reserve tickets in advance.
USD25, 4h

1:30pm

Lunch at Joe’s Shanghai

Renowned for soup dumplings in Chinatown, open till 10pm.
USD25, 1h

3:00pm

Walk the High Line

A unique elevated park offering views of the Hudson River, open 7am to 11pm.
USD0, 2h

6:00pm

Dinner at Carbone

Upscale Italian-American restaurant with iconic dishes, reservation recommended, open till 11pm.
USD60, 2h
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Day 8: More NYC Highlights

New York City, United States on July 23, 2025

8:00am

Breakfast at Buvette

Charming French café with delicious pastries, open 7am to 3pm.
USD20, 1h

9:30am

Visit the MET (Metropolitan Museum of Art)

World-class art museum open 10am to 5:30pm with vast collections.
USD30, 3h

1:00pm

Lunch at Shake Shack

Popular burger chain in Central Park area, open till late.
USD15, 1h

2:30pm

Central Park stroll and visit Bethesda Terrace

Iconic park with gardens, lakes and landmarks, open dawn to dusk.
USD0, 2h

5:30pm

Visit Top of the Rock

Observation deck with panoramic city views, open until midnight.
USD40, 1.5h

7:30pm

Dinner at Totto Ramen

Highly-rated ramen spot with traditional Japanese noodles, open till 10pm.
USD25, 1.5h
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Day 9: Niagara Falls Adventure

Niagara Falls, United States on July 24, 2025

7:00am

Early Breakfast at Hotel

Quick breakfast to gear up for the drive to Niagara Falls.
USD15, 1h

8:00am

Drive to Niagara Falls

Approximate 6.5-hour drive from NYC to Niagara Falls, take breaks en route.
USD65 fuel, 6.5h

2:30pm

Lunch at The Red Coach Inn

Historic dining with views near the falls, open till 8pm.
USD30, 1.5h

4:00pm

Maid of the Mist Boat Tour

Iconic boat tour to experience the falls up-close, open 9am to 7pm July season.
USD25, 1.5h

6:00pm

Explore Niagara Falls State Park

Walk scenic trails and viewpoints around the falls, open 24 hours.
USD0, 1.5h

8:00pm

Dinner at Hard Rock Cafe Niagara Falls

Casual dining with classic American fare near the falls, open till late.
USD35, 2h
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Day 10: Ohio Exploration

Ohio, United States on July 25, 2025

7:00am

Breakfast at Hotel

Get a filling breakfast before departure to Ohio.
USD15, 1h

8:00am

Drive to Cleveland, Ohio

Approximate 3-hour drive to Cleveland, home of Rock & Roll Hall of Fame.
USD35 fuel, 3h

11:30am

Visit Rock & Roll Hall of Fame

Explore exhibits on music legends and history, open 10am to 5:30pm.
USD35, 2h

1:30pm

Lunch at West Side Market Café

Enjoy fresh food in historic market setting, open till 3pm weekdays.
USD20, 1h

3:00pm

Walk along the Cleveland Waterfront

Relax with views of Lake Erie and city skyline, open all day.
USD0, 2h

6:30pm

Dinner at Slyman's Restaurant

Famous for generous corned beef sandwiches, open till 8pm.
USD20, 1.5h
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Day 11: Chicago Arrival

Chicago, United States on July 26, 2025

7:00am

Breakfast at Hotel

Prepare with breakfast before the drive to Chicago.
USD15, 1h

8:00am

Drive to Chicago

Approximate 5.5-hour drive from Cleveland to Chicago, enjoy scenic stops if wished.
USD55 fuel, 5.5h

2:00pm

Lunch at Lou Malnati’s Pizzeria

Relish famous Chicago deep-dish pizza, open from 11am to 10pm.
USD25, 1.5h

4:00pm

Visit Millennium Park

See iconic Cloud Gate sculpture and gardens, park open 6am to 11pm.
USD0, 2h

7:00pm

Dinner at Girl & The Goat

Highly acclaimed restaurant with bold flavours, booking recommended, open until 10:30pm.
USD50, 2h
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Day 12: Chicago Highlights

Chicago, United States on July 27, 2025

8:00am

Breakfast at Wildberry Pancakes and Cafe

Popular spot for pancakes and hearty breakfast, opening from 7am.
USD20, 1h

9:30am

Visit Art Institute of Chicago

One of the world’s great art museums, open 10:30am to 5pm, closed Tuesdays.
USD25, 3.5h

1:30pm

Lunch at Portillo’s

Famous for Chicago-style hot dogs and Italian beef sandwiches, open till 10pm.
USD15, 1h

3:00pm

Architectural River Cruise

Guided boat tour showcasing Chicago’s iconic architecture, cruises run daily from 10am to 7pm.
USD45, 1.5h

6:00pm

Dinner at The Purple Pig

Mediterranean-inspired small plates in a lively setting, open until 11pm.
USD40, 2h
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Day 13: Return to Maryland

Maryland, United States on July 28, 2025

8:00am

Breakfast at Hotel

Enjoy a final Chicago breakfast before the drive back.
USD15, 1h

9:00am

Drive to Maryland

Long drive back to Maryland from Chicago approximately 11-12 hours, plan breaks accordingly.
USD110 fuel, 12h

9:00pm

Dinner at Home in Maryland

Arrive and enjoy a quiet home-cooked meal after the long journey.
USD0, 1.5h
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Day 14: Recovery and Family Time

Maryland, United States on July 29, 2025

9:00am

Breakfast at Home

Relaxed breakfast with family to recover from travel fatigue.
USD0, 1h

10:30am

Relaxation and family visits

Spend the day leisurely bonding and enjoying home comforts.
USD0, All day

7:00pm

Dinner at Home

Enjoy a final family dinner before departure.
USD0, 2h
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