Cleveland, Ohio 20-Day Trip Itinerary

Depart Chicago

Begin your exciting road trip from Chicago, heading east towards Cleveland, Ohio.

Ensure the car is packed with snacks, entertainment for the children, and any necessary travel documents. Plan for stops every 2-3 hours.

Bring a cooler with drinks and snacks. Have playlists or audiobooks ready for the drive. Download offline maps in advance.

Arrive & Check-in

Arrive in Cleveland, check into your accommodation, and allow everyone to settle in after the drive.

Unpack, freshen up, and let the children relax before dinner.

Family Welcome Dinner

Enjoy a relaxed family dinner at a local restaurant in Cleveland to celebrate the start of your adventure.

Many family-friendly dining options are available downtown, ranging from casual eateries to sit-down restaurants. Consider checking out establishments near your hotel or popular areas like East 4th Street.

Rock & Roll Hall of Fame

Immerse yourselves in the history of rock and roll at this iconic museum.

Explore exhibits on legendary artists, artifacts, and interactive displays that appeal to all ages.

Book tickets online in advance to save time. Allow ample time for younger visitors to enjoy the more interactive exhibits.

Explore North Coast Harbor

Enjoy a leisurely stroll around North Coast Harbor, right outside the Rock & Roll Hall of Fame.

Take in views of Lake Erie and the Cleveland skyline.

A great spot for photos and fresh air. There are often various events or seasonal attractions here.

Dinner in The Flats

Dine in The Flats, a vibrant entertainment district along the Cuyahoga River, offering a variety of restaurants with waterfront views.

Cleveland Museum of Natural History

Explore dinosaur skeletons, discover Ohio's natural history, and visit the live animal exhibits.

This museum offers engaging educational experiences for all ages.

Highlights include 'Lucy,' the famous hominid fossil, and various wildlife exhibits. Check for any special temporary exhibits.

Cleveland Botanical Garden

Wander through diverse indoor and outdoor gardens, including a stunning glasshouse with a Costa Rican rainforest and a desert environment. A peaceful and beautiful stop for the family.

Offers a nice change of pace and a chance for children to explore nature in a controlled environment, especially the butterfly garden.

Dinner in University Circle

Enjoy dinner in the vibrant University Circle district, which offers a variety of dining options from casual to upscale, catering to diverse tastes.

Great Lakes Science Center

A highly interactive science museum perfect for children.

Explore hands-on exhibits focusing on science, technology, and engineering, including the NASA Glenn Visitor Center.

Children will love the numerous interactive displays and experiments. Check the schedule for live demonstrations.

Cleveland Metroparks Lakefront Reservation

Enjoy some outdoor time at one of Cleveland's beautiful lakefront parks.

Depending on the weather, you can walk, play at a playground, or simply take in the views of Lake Erie.

Great for letting the children burn off some energy. Dress in layers, as it can be windy by the lake.

Dinner in Little Italy

Experience the charm and delicious cuisine of Cleveland's historic Little Italy.

Enjoy authentic Italian dishes in a cozy, family-friendly atmosphere.

Don't forget to grab some cannoli or gelato for dessert!

West Side Market

Visit Cleveland's historic West Side Market, an iconic indoor/outdoor market featuring over 100 vendors selling meats, seafood, produce, baked goods, and prepared foods.

A treat for the senses and a great place to grab lunch or snacks.

Encourage children to try new foods. It's a vibrant, bustling environment perfect for experiencing local culture.

Explore Ohio City

Spend some time exploring the charming Ohio City neighborhood, known for its Victorian architecture, independent shops, and craft breweries (for the adults, perhaps a quick stop at a kid-friendly spot).

Enjoy a leisurely walk, browse local shops, or find a comfortable cafe.

Relaxation & Free Time

Enjoy some free time for relaxation at the hotel, allow children to play, or revisit a favorite spot in Cleveland.

This provides flexibility and prevents over-scheduling.

Use this time for souvenir shopping, swimming (if your hotel has a pool), or simply unwinding before dinner.

Farewell Cleveland Dinner

Enjoy a final family dinner in Cleveland, reflecting on your experiences before heading to your next destination.

Drive to Pittsburgh

Enjoy the scenic drive from Cleveland, Ohio to Pittsburgh, Pennsylvania.

Grab snacks and make a comfort stop along the way.

Hotel Check-in & Lunch

Check into your Pittsburgh accommodation and settle in.

Grab a quick lunch at a local eatery near your hotel.

The Andy Warhol Museum

Explore the largest museum dedicated to a single artist in North America.

Engage with the iconic pop art of Andy Warhol, a Pittsburgh native.

Great for older children and adults. Check for family-friendly programs or interactive exhibits.

Dinner in Cultural District

Enjoy dinner in Pittsburgh's vibrant Cultural District, offering a variety of dining options.

Carnegie Science Center

Spend the morning at the Carnegie Science Center, featuring four floors of interactive exhibits, a planetarium, and an Omnimax theater.

Engaging for all ages.

Allow plenty of time, especially with children. Consider catching a live science demonstration.

Lunch at Science Center

Have lunch at the cafe within the Carnegie Science Center or a nearby casual spot.

Duquesne Incline & Views

Ride the historic Duquesne Incline up Mount Washington for breathtaking panoramic views of Pittsburgh's skyline, rivers, and bridges.

A unique historical experience and a fantastic photo opportunity. The observation deck at the top is a must-see.

Dinner in Station Square

Dine at one of the many restaurants in Station Square, a lively entertainment complex at the base of Mount Washington.

Phipps Conservatory

Explore the beautiful Phipps Conservatory and Botanical Gardens.

Wander through diverse plant collections, seasonal flower shows, and a children's discovery garden.

A peaceful and visually stunning experience, great for children to learn about nature.

Lunch in Oakland

Grab a casual lunch in the Oakland neighborhood, home to Phipps Conservatory and several universities, offering many student-friendly eateries.

Point State Park

Visit Point State Park, a National Historic Landmark at the confluence of Pittsburgh's three rivers.

Enjoy the fountain, open spaces, and learn about its historical significance.

Perfect for kids to run around and enjoy the river views. There are walking paths and often events.

Dinner Downtown

Explore more dining options in Downtown Pittsburgh, perhaps trying a cuisine you haven't had yet.

Carnegie Museum of Natural History

Delve into the wonders of the natural world with dinosaur skeletons, impressive gem collections, and exhibits on animal life and ecosystems.

Highly engaging for children with its dinosaur hall. Consider purchasing a joint ticket with the Carnegie Museum of Art if time allows.

Quick Lunch in Oakland

Enjoy a quick and casual lunch in the Oakland area before heading to your next stop.

Explore Strip District

Wander through the historic Strip District, a vibrant market neighborhood.

Discover ethnic food stores, produce stands, unique boutiques, and cafes.

Great for unique souvenirs and trying different snacks. It's a lively area with lots to see and smell.

Dinner in the Strip District

Enjoy dinner at one of the Strip District's diverse restaurants, from Italian delis to seafood spots.

Morning Leisure & Park Visit

Enjoy a relaxed morning.

Perhaps visit a local park like Schenley Park for some outdoor playtime or a gentle stroll, or revisit a favorite spot for last-minute souvenirs.

Schenley Park offers playgrounds, trails, and open spaces, perfect for children to burn off some energy.

Farewell Lunch in Pittsburgh

Enjoy one last delicious meal in Pittsburgh, perhaps trying a classic Pittsburgh sandwich like a Primanti Bros.

sandwich.

Primanti Bros. is a Pittsburgh institution known for sandwiches with fries and coleslaw right on them.

Prepare for Departure

Return to the hotel to pack up, check out, and prepare for the next leg of your road trip to Lancaster County.

Ensure all belongings are packed and the car is ready for travel.

Drive from Pittsburgh to Lancaster

Enjoy the scenic drive across Pennsylvania to Lancaster County.

Pack snacks and consider podcasts or audiobooks for the kids.

There will be several rest stops available along the Pennsylvania Turnpike. Tolls will apply on the turnpike.

Hotel Check-in

Check into your family-friendly accommodation in Lancaster and settle in after the drive.

Amish Farm & House Visit

Take a guided tour of an authentic Amish house and farm, offering a fascinating introduction to the Amish way of life, complete with farm animals and craft demonstrations.

Tours are family-friendly and highly informative. Check their website for specific tour times and availability in early March.

Family-Style Amish Dinner

Enjoy a traditional Pennsylvania Dutch dinner at a family-style restaurant, known for hearty portions and classic comfort food.

Great for families with children, often offering all-you-can-eat options. Reservations are often a good idea.

Authentic Amish Buggy Ride

Experience the peaceful Lancaster County countryside with a traditional horse-and-buggy ride, often narrated by an Amish or Mennonite guide sharing insights into their culture.

Offers various lengths of rides; choose one suitable for children. Dress warmly if it's a cool March day.

Lunch at a Local Amish Market

Visit a bustling local market (like Bird-in-Hand Farmers Market or Kitchen Kettle Village) for fresh baked goods, sandwiches, and local produce.

Markets offer a great opportunity to sample local treats and find unique souvenirs. Check opening days, as some are not open daily.

Explore Kitchen Kettle Village

Wander through a village of shops, selling local jams, relishes, handmade crafts, and more.

Kids might enjoy the various food samples and unique items.

Free to enter and browse. There are often opportunities to see artisans at work.

Visit a Family Petting Farm

Enjoy interaction with farm animals at a family-friendly petting farm, offering a hands-on experience for children.

A relaxed outdoor activity that kids of all ages usually love. Check opening times.

Dinner at a Local Restaurant

Savor another delicious meal at a local restaurant offering a mix of American and Pennsylvania Dutch cuisine.

Explore options like Miller's Smorgasbord for another family-style experience, or a casual diner.

Explore Quaint Lititz, PA

Discover the charming town of Lititz, known for its unique shops, historic architecture, and recognition as 'America's Coolest Small Town'.

Stroll down Main Street and browse.

Plenty of independent shops, cafes, and historic sites. Parking is available.

Wilbur Chocolate Co. Store

Visit the famous Wilbur Chocolate Co.

Retail Store in Lititz, where you can find delicious chocolates, observe chocolate-making through a viewing window, and learn about its history.

Great for a sweet treat and a bit of local history. Kids will love the samples!

Lunch in Lititz

Enjoy a casual lunch at one of Lititz's many eateries, from cafes to sandwich shops.

Consider options along Main Street or Broad Street.

Julius Sturgis Pretzel Bakery Tour

Take a fun and interactive tour of America's first commercial pretzel bakery, learning the history of pretzels and even trying your hand at twisting your own pretzel.

Reservations are highly recommended as tours can fill up quickly. A great hands-on activity for kids.

Dinner in Lancaster City

Explore dinner options in downtown Lancaster, which offers a diverse range of restaurants from casual to upscale.

Consider restaurants along Queen Street or Duke Street.

Self-Guided Covered Bridge Tour

Embark on a scenic drive through Lancaster County to discover its picturesque covered bridges.

Many maps are available online or at visitor centers.

Enjoy the beauty of the countryside and the historical charm of these unique bridges. Great for photo opportunities.

Picnic Lunch in a Scenic Spot

Enjoy a packed picnic lunch from a local deli or market amidst the beautiful Lancaster countryside, perhaps near a covered bridge or park.

A relaxing way to enjoy the scenery. Grab supplies from Central Market or a local grocery store.

Fun at Long's Park

Spend the afternoon at Long's Park, a large community park featuring extensive playgrounds, walking trails, a petting zoo, and ample space for kids to run around.

A perfect spot for families to unwind, play, and enjoy some fresh air. The petting zoo is a highlight for younger children.

Pennsylvania Dutch Dinner

Conclude your day with another authentic Pennsylvania Dutch dinner, experiencing the rich culinary traditions of the region.

Known for family-style dining and a truly immersive PA Dutch meal. Great for trying various local dishes.

Explore Central Market Lancaster

Visit the historic Central Market, the oldest continuously operating farmers market in the U.

S. Browse fresh produce, local foods, baked goods, and crafts. Great for breakfast or snacks.

A vibrant community hub, perfect for experiencing local life and grabbing some last-minute treats. Check market days; it's typically open Tuesday, Friday, and Saturday mornings.

Last-Minute Souvenir Shopping

Pick up any last souvenirs or local products to remember your time in Lancaster County.

Look for unique Amish crafts, local food products, or gifts.

Farewell Lunch in Lancaster

Enjoy a final lunch in Lancaster, perhaps at a cafe or restaurant you've enjoyed or want to try one last time.

A good opportunity to revisit a favorite or try a new spot.

Pack & Relax for DC Journey

Return to your accommodation to pack up, ensure everything is ready for departure to Washington D.

C. tomorrow, and enjoy some downtime.

Prepare snacks and entertainment for the drive to D.C. tomorrow.

Drive to Washington D.C.

Enjoy the scenic drive from Lancaster County, Pennsylvania, to Washington D.

C., marking the final leg of your family's road trip.

Plan for rest stops as needed during the drive. Traffic can be heavy approaching D.C.

Lunch upon Arrival

Grab a quick and casual lunch in the Penn Quarter or downtown D.

C. area after settling in.

Many options available, from delis to family-friendly restaurants.

Hotel Check-in & Refresh

Check into your accommodation and take some time to refresh before starting your D.

C. exploration.

Official check-in time is often 3 PM. Confirm with the hotel if early check-in is possible.

Old Town Trolley Tour

Embark on a narrated sightseeing tour of Washington D.

C.'s famous monuments and memorials, offering an excellent overview of the city.

This tour is a great way to orient yourselves and see many key sights without excessive walking on your first day. Book tickets in advance.

Dinner in Penn Quarter

Enjoy a family dinner in the lively Penn Quarter neighborhood, known for its diverse dining options.

Consider options near Capital One Arena for a variety of choices.

National Mall Monuments Walk

Walk along the iconic National Mall, visiting the Washington Monument (exterior), World War II Memorial, Reflecting Pool, and Lincoln Memorial.

This area is rich with history and offers stunning views.

Wear comfortable shoes! Consider renting scooters or bikes for part of the journey if children get tired, though Unlimited Biking is planned for Day 18.

Lunch near the National Mall

Enjoy lunch from one of the many food trucks or casual eateries surrounding the National Mall.

Food trucks offer diverse and quick options. Look for spots near the museums.

National Museum of Natural History

Explore the Smithsonian National Museum of Natural History, featuring dinosaur exhibits, the Hope Diamond, and fascinating displays about the natural world.

Admission is free.

One of the most popular Smithsonian museums, great for all ages. Check their website for current exhibitions.

Stroll Past National Archives

Take a leisurely walk past the National Archives Building and learn about where the U.

S. Constitution, Declaration of Independence, and Bill of Rights are housed.

Consider visiting the interior another time if your family is interested in seeing the founding documents up close (requires timed passes).

Dinner in Georgetown

Experience the charming historic neighborhood of Georgetown with a family dinner.

Explore M Street for shopping and dining.

Georgetown is easily accessible by bus or a short taxi/rideshare from downtown.

The Phillips Collection

Visit America's first museum of modern art, housed in an intimate setting.

Features works by Renoir, Rothko, and Bonnard. A calm and enriching cultural experience.

A manageable size for families. Consider checking their family programs or specific exhibits suitable for children.

Lunch in Dupont Circle

Enjoy lunch in the vibrant Dupont Circle neighborhood, known for its diverse restaurants and cafes.

Walk around Dupont Circle itself after lunch, a popular gathering spot with a fountain.

Unlimited Biking Washington DC

Rent bikes for the family, including kids' bikes and trailers, and explore the city's scenic paths, perhaps around the Tidal Basin or Rock Creek Park.

A fantastic way to see D.C. at your own pace and get some exercise. Helmets and locks usually included. Book in advance, especially for specific bike sizes.

Relax at Farragut Square

Unwind with a stroll or sit-down at Farragut Square, a lovely urban park perfect for people-watching and a moment of relaxation.

A popular spot for locals, often has food vendors during weekdays.

Dinner in Dupont Circle

Enjoy another evening meal in Dupont Circle, trying a different restaurant or revisiting a favorite.

Consider ethnic cuisine options in this diverse neighborhood.

U.S. Capitol & Library of Congress

View the iconic U.

S. Capitol Building from the outside and explore the exterior of the magnificent Library of Congress, which offers stunning architecture and historical exhibits.

Consider booking a timed tour of the U.S. Capitol in advance if your family is interested in an interior visit. The Library of Congress is free to enter and explore some areas.

Lunch on Capitol Hill

Enjoy lunch in the Capitol Hill neighborhood, with options ranging from casual cafes to more upscale dining.

Explore Eastern Market if time permits, for a vibrant food and craft scene.

National Air and Space Museum

Immerse yourselves in the history of flight and space exploration at the Smithsonian National Air and Space Museum.

Features iconic aircraft, spacecraft, and interactive exhibits. Admission is free.

This museum is incredibly popular, so arrive early or be prepared for crowds. Check their website for any timed entry requirements.

White House Exterior View

Walk to the White House and view the Executive Residence from Lafayette Square (North Lawn) or the Ellipse (South Lawn).

For security reasons, public tours of the White House must be requested through your Member of Congress well in advance (3 months +).

Farewell Dinner

Enjoy a special farewell dinner in a D.

C. neighborhood of your choice, reflecting on your amazing 20-day road trip.

Consider dining near your hotel or in a favorite area like Penn Quarter or Dupont Circle.

Breakfast & Packing

Enjoy a final breakfast in D.

C. and finish packing for your departure.

Many hotels offer grab-and-go options or have an on-site restaurant.

Last-Minute Souvenir Shopping

Visit a gift shop near your hotel or a favorite museum for any last-minute souvenirs to remember your trip.

The Smithsonian museums have excellent gift shops.

Hotel Check-out

Complete the check-out process from your hotel.

Standard check-out time is usually 11 AM or 12 PM. Confirm with the front desk.

Begin Drive Home

Start your journey home from Washington D.

C., concluding your memorable 20-day road trip.

Plan your route and potential overnight stops if driving all the way back to Chicago. This marks the end of the planned 20-day itinerary activities.