29 days in Midwest Itinerary

29 days in Midwest Itinerary

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Route & dates

29 days in Midwest Itinerary

Start: Columbia
Fly:  5​h 15​min
Indianapolis
— 2 nights
Drive:  2​h
Dayton
— 1 night
Drive:  2​h
Rockbridge
— 2 nights
Drive:  3​h 15​min
Cleveland
— 3 nights
Fly:  3​h 30​min
Saint Louis
— 4 nights
Fly + Drive:  3​h 45​min
Branson
— 3 nights
Drive:  3​h 45​min
Kansas City
— 3 nights
Fly:  4​h 15​min
Chicago
— 6 nights
subway + Fly:  3​h
Green Bay
— 2 nights
Fly + taxi:  5​h 15​min
Custer
— 2 nights
taxi + Fly:  6​h 30​min
End: Columbia

2
nights
Indianapolis

Indianapolis ©
Indiana's capital and most populous city, Indianapolis is best known for its racecar events and impressive museums, and as the hometown of Kurt Vonnegut.
Start off your visit on the 2nd (Fri): have some family-friendly fun at Bad Axe Throwing. On the 3rd (Sat), you'll have a packed day of sightseeing: have fun at Lucas Oil Stadium, have fun and explore at Children's Museum of Indianapolis, then test your team's savvy at popular escape rooms, and finally indulge your taste buds at Rocket Fizz.

To find traveler tips, maps, more things to do, and other tourist information, use the Indianapolis trip planner .

Columbia to Indianapolis is an approximately 5.5-hour flight. You can also drive; or take a bus. In November, Indianapolis is little chillier than Columbia - with highs of 52°F and lows of 34°F. Finish your sightseeing early on the 4th (Sun) to allow enough time to drive to Dayton.

Things to do in Indianapolis

#Fun & Games, #Outdoors, #Parks
Highlights from your plan
Bad Axe Throwing ©
Bad Axe Throwing
Room Escape Games
Victory Field ©
Victory Field

1
night
Dayton

Dayton ©
Home of airplane pioneers the Wright brothers, Dayton prides itself on its inventors, including Charles F.
On the 5th (Mon), admire the natural beauty at Wegerzyn Gardens MetroPark, then examine the collection at National Museum of the U.S. Air Force, then contemplate the long history of Carillon Historical Park, and finally have some family-friendly fun at Miami Valley Gaming.

To find other places to visit, where to stay, more things to do, and tourist information, use the Dayton trip itinerary planning site .

Traveling by car from Indianapolis to Dayton takes 2 hours. Alternatively, you can take a bus. In November, daily temperatures in Dayton can reach 52°F, while at night they dip to 34°F. Finish your sightseeing early on the 5th (Mon) to allow enough time to drive to Rockbridge.

Things to do in Dayton

#Fun & Games, #Historic Sites, #Museums

Side Trip

Miami Valley Gaming
Highlights from your plan
National Museum of the U.S. Air Force ©
Miami Valley Gaming ©
Miami Valley Gaming
Carillon Historical Park ©
Carillon Historical Park

2
nights
Rockbridge

Rockbridge is an unincorporated community in eastern Good Hope Township, Hocking County, Ohio, United States. Kick off your visit on the 6th (Tue): kick your exploration up a notch at some of the top local zipline courses and adventure parks, look for all kinds of wild species at Conkles Hollow State Nature Preserve, and then explore the fascinating underground world of Ash Cave. On the 7th (Wed), you'll have a packed day of sightseeing: take in the architecture and atmosphere at St. Thomas Aquinas Church, take in nature's colorful creations at Dawes Arboretum, and then delve into the distant past at Great Circle Earthworks.

To find photos, reviews, and tourist information, go to the Rockbridge holiday maker site .

Drive from Dayton to Rockbridge in 2 hours. In November in Rockbridge, expect temperatures between 52°F during the day and 32°F at night. Finish your sightseeing early on the 7th (Wed) so you can drive to Cleveland.

Things to do in Rockbridge

#Parks, #Historic Sites, #Wildlife

Side Trips

Dawes Arboretum, St. Thomas Aquinas Church, Great Circle Earthworks, Ash Cave
Highlights from your plan
Zipline
Conkles Hollow State Nature Preserve ©
Ash Cave ©
Ash Cave

3
nights
Cleveland

Cleveland ©
A culturally diverse city situated on the shores of Lake Erie, Cleveland boasts many places to visit, such as world-class museums, popular amusement parks, and sprawling recreational areas.
Change things up with these side-trips from Cleveland: F.A. Seiberling Nature Realm (in Akron) and Cedar Point (in Sandusky). And it doesn't end there: admire the masterpieces at The Cleveland Museum of Art, see the interesting displays at Rock & Roll Hall of Fame, pause for some serene contemplation at St John's Cathedral, and tour the pleasant surroundings at Cleveland Metroparks.

For photos, maps, traveler tips, and tourist information, use the Cleveland trip itinerary builder app .

Drive from Rockbridge to Cleveland in 3.5 hours. Alternatively, you can do a combination of taxi and bus; or do a combination of taxi and bus. Traveling from Rockbridge in November, Cleveland is a bit warmer at night with lows of 39°F. Wrap up your sightseeing on the 10th (Sat) to allow time to travel to Saint Louis.

Things to do in Cleveland

#Parks, #Fun & Games, #Theme Parks

Side Trips

Bay Lanes Bowling, F.A. Seiberling Nature Realm, Cedar Point
Highlights from your plan
The Cleveland Museum of Art ©
The Cleveland Museum of Art
Cedar Point ©
Cedar Point
Rock & Roll Hall of Fame ©
Rock & Roll Hall of Fame

4
nights
Saint Louis

Saint Louis ©
Test the local claim that Saint Louis is second only to Washington, D.C.
Change things up with these side-trips from Saint Louis: River City Rascals (in O'Fallon) and Pinckney Bend Distillery (in New Haven). The adventure continues: enjoy breathtaking views from The Gateway Arch, admire nature's wide array of creatures at Saint Louis Zoo, contemplate the long history of Cahokia Mounds State Historic Site, and see the interesting displays at City Museum.

To see photos, where to stay, maps, and other tourist information, read our Saint Louis road trip tool .

Traveling by flight from Cleveland to Saint Louis takes 3.5 hours. Alternatively, you can drive; or take a bus. The time zone changes from Eastern Standard Time (EST) to Central Standard Time (CST), which is usually a -1 hour difference. November in Saint Louis sees daily highs of 56°F and lows of 35°F at night. Cap off your sightseeing on the 14th (Wed) early enough to travel to Branson.

Things to do in Saint Louis

#Parks, #Historic Sites, #Outdoors

Side Trips

Cahokia Mounds State Historic Site, River City Rascals, Pinckney Bend Distillery
Highlights from your plan
Cathedral Basilica of Saint Louis ©
Cathedral Basilica of Saint Louis
The Gateway Arch ©
The Gateway Arch
Saint Louis Zoo ©
Saint Louis Zoo

3
nights
Branson

Branson ©
Nestled in Missouri's beautiful Ozark Mountains lies one of the country's most attractive vacation towns for year-round family entertainment.
Plan for a day of cool, family-friendly fun on the 15th (Thu) at Silver Dollar City. There's much more to do: contemplate the waterfront views at Table Rock Lake, see the interesting displays at Titanic Museum, identify plant and animal life at Shepherd of the Hills Fish Hatchery, and get great views at College of the Ozarks.

To find out how to plan a trip to Branson, use our trip itinerary maker.

Do a combination of flight and car from Saint Louis to Branson in 4 hours. Alternatively, you can drive; or do a combination of bus and taxi. In November, plan for daily highs up to 58°F, and evening lows to 38°F. Finish up your sightseeing early on the 17th (Sat) so you can go by car to Kansas City.

Things to do in Branson

#Parks, #Theme Parks, #Wildlife

Side Trips

Table Rock Lake, National Tiger Sanctuary
Highlights from your plan
Escape Code ©
Escape Code
Silver Dollar City ©
Silver Dollar City
Table Rock Lake ©
Table Rock Lake

3
nights
Kansas City

Kansas City ©
The largest municipality in Missouri, Kansas City has an impressive array of world-class museums, shopping areas, and great places to eat, all of which attract tourism to the area.
Go for a jaunt from Kansas City to Weston to see Holladay Distillery about 42 minutes away. There's still lots to do: test your team's savvy at popular escape rooms, explore the world behind art at The Nelson-Atkins Museum of Art, admire all the interesting features of Children's Mercy Park, and look for gifts at Kansas City River Market.

To see reviews, where to stay, photos, and other tourist information, go to the Kansas City holiday maker app .

Traveling by car from Branson to Kansas City takes 4 hours. Alternatively, you can take a bus; or do a combination of bus and train. November in Kansas City sees daily highs of 56°F and lows of 38°F at night. Wrap up your sightseeing on the 20th (Tue) early enough to travel to Chicago.

Things to do in Kansas City

#Museums, #Parks, #Breweries

Side Trips

Kansas City, Harry S. Truman Library and Museum, Deanna Rose Children's Farmstead, Holladay Distillery
Highlights from your plan
Holladay Distillery ©
Holladay Distillery
Room Escape Games
National WWI Museum and Memorial ©
National WWI Museum and Memorial

6
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
When in Chicago, make a side trip to see Bengtson's Pumpkin Farm in Homer Glen, approximately 42 minutes away. And it doesn't end there: admire the masterpieces at The Art Institute of Chicago, see the interesting displays at The Field Museum, get curious at Museum of Science and Industry, and meet the residents at Lincoln Park Zoo.

To see where to stay and tourist information, go to the Chicago trip planner.

Getting from Kansas City to Chicago by flight takes about 4.5 hours. Other options: take a train; or drive. Expect a bit cooler weather when traveling from Kansas City in November: highs in Chicago hover around 50°F, while lows dip to 35°F. Wrap up your sightseeing on the 26th (Mon) to allow time to travel to Green Bay.

Things to do in Chicago

#Museums, #Outdoors, #Parks

Side Trip

Bengtson's Pumpkin Farm
Highlights from your plan
The Art Institute of Chicago ©
The Art Institute of Chicago
Millennium Park ©
Millennium Park
Museum of Science and Industry ©
Museum of Science and Industry

2
nights
Green Bay

Green Bay ©
Home of the Green Bay Packers, the city of Green Bay centers around sports and is home to hundreds of notable football icons, including Brett Favre and Curly Lambeau.
Start off your visit on the 27th (Tue): look for gifts at Seroogy's Chocolates, take in nature's colorful creations at Green Bay Botanical Garden, then admire all the interesting features of Lambeau Field, and finally examine the collection at Green Bay Packer Hall of Fame. Here are some ideas for day two: learn about winemaking at Von Stiehl Winery and then find something for the whole family at Bay Beach Amusement Park.

For ratings, maps, and more tourist information, read Green Bay planning site .

Getting from Chicago to Green Bay by combination of subway and flight takes about 3 hours. Other options: drive; or do a combination of flight and bus. Traveling from Chicago in November, things will get slightly colder in Green Bay: highs are around 45°F and lows about 29°F. Cap off your sightseeing on the 28th (Wed) early enough to travel to Custer.

Things to do in Green Bay

#Theme Parks, #Parks, #Wineries

Side Trips

Von Stiehl Winery, Seroogy's Chocolates
Highlights from your plan
Lambeau Field ©
Lambeau Field
Green Bay Botanical Garden ©
Green Bay Botanical Garden
Green Bay Packer Hall of Fame ©
Green Bay Packer Hall of Fame

2
nights
Custer

Custer ©
Generally considered to be the oldest town established by European Americans in the Black Hills, Custer began as a mining town.
On the 29th (Thu), admire the majestic nature at Custer State Park, then take a memorable drive along Iron Mountain Road, then explore the striking landscape of Mount Rushmore National Memorial, and finally pause for some photo ops at Crazy Horse Memorial. Get ready for a full day of sightseeing on the 30th (Fri): explore the activities along Sylvan Lake and then take in the dramatic natural features at Needles Eye Tunnel.

To find other places to visit, maps, ratings, and other tourist information, use the Custer journey builder tool .

You can do a combination of flight and taxi from Green Bay to Custer in 5.5 hours. Other options are to do a combination of bus, flight, and taxi; or drive. You'll gain 1 hour traveling from Green Bay to Custer due to the time zone difference. Traveling from Green Bay in November, Custer is a bit cooler at night with lows of 23°F. Wrap up your sightseeing on the 30th (Fri) to allow time to travel back home.

Things to do in Custer

#Parks, #Nature, #Outdoors

Side Trips

Crazy Horse Memorial, Mount Rushmore National Memorial
Highlights from your plan
Mount Rushmore National Memorial ©
Mount Rushmore National Memorial
Custer State Park ©
Custer State Park
Needles Eye Tunnel ©
Needles Eye Tunnel

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