11 days in Charlottesville & Iowa Itinerary

11 days in Charlottesville & Iowa Itinerary

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Route & dates

11 days in Charlottesville & Iowa Itinerary

Start: New York City
Fly:  3 h 30 min
1
Charlottesville
— 6 nights
Fly:  6 h 45 min
2
Dubuque
— 1 night
Drive:  1 h 30 min
3
West Branch
— 1 night
Drive:  2 h 45 min
4
Mason City
— 1 night
Drive:  2 h 30 min
5
Winterset
— 1 night
+2
Drive + Fly + Drive:  6 h 15 min
End: New York City

6
nights
Charlottesville

Charlottesville ©
Situated at the foothills of the Blue Ridge Mountains, Charlottesville is perhaps best known as the home of three of the United States' founding fathers, including Thomas Jefferson.
Get some historical perspective at Frontier Culture Museum and The Glass Palette - Interactive Glass Art Studio. Lee Chapel and Museum and Hugh Mercer Apothecary Shop will appeal to museum buffs. Explore the numerous day-trip ideas around Charlottesville: Crabtree Falls (in Wintergreen), Appomattox (McLean House, Appomattox Court House National Historical Park, &more) and Canal Basin Square (in Scottsville). Next up on the itinerary: contemplate the long history of Stonewall Jackson House, get engrossed in the history at The Rising Sun Tavern, sample the fine beverages at Copper Fox Distillery, and see the interesting displays at Woodrow Wilson Presidential Library and Museum.

For reviews, maps, more things to do, and tourist information, read Charlottesville online vacation builder.

New York City to Charlottesville is an approximately 3.5- hour flight. You can also do a combination of train and flight; or drive. Traveling from New York City in September, plan for a bit cooler nights in Charlottesville, with lows around 60°F. Cap off your sightseeing on the 27th (Sun) early enough to travel to Dubuque.

Things to do in Charlottesville

Historic Sites Museums Nature

Side Trips

Fredericksburg, Appomattox, Sperryville, Lexington, Staunton
Highlights from your plan
Mulberry Row ©
Mulberry Row
Frontier Culture Museum ©
Frontier Culture Museum
Lee Chapel and Museum ©
Lee Chapel and Museum

1
night
Dubuque

Dubuque ©
Dubuque is the county seat of Dubuque County, Iowa, United States, located along the Mississippi River. Start off your visit on the 28th (Mon): admire the natural beauty at Dubuque Arboretum and Botanical Gardens, then stroll around Eagle Point Park, then learn about winemaking at Stone Cliff Winery, and finally make a trip to Fenelon Place Elevator Co..

For ratings, other places to visit, where to stay, and more tourist information, use the Dubuque trip itinerary planning site.

Fly from Charlottesville to Dubuque in 7 hours. Alternatively, you can drive; or do a combination of train, subway, and bus. The time zone changes from Eastern Standard Time to Central Standard Time, which is usually a -1 hour difference. Prepare for a bit cooler weather when traveling from Charlottesville in September: high temperatures in Dubuque hover around 75°F and lows are around 54°F. Wrap up your sightseeing on the 28th (Mon) early enough to drive to West Branch.

Things to do in Dubuque

Parks Wineries
Highlights from your plan
Eagle Point Park ©
Eagle Point Park
Stone Cliff Winery ©
Stone Cliff Winery
Dubuque Arboretum and Botanical Gardens ©

1
night
West Branch

West Branch ©
West Branch is a city in Cedar and Johnson counties in the U.S. On the 29th (Tue), try your luck at Riverside Casino & Golf Resort, then steep yourself in history at Herbert Hoover National Historic Site, and then get advice or help at Herbert Hoover Presidential Library and Museum.

For reviews, other places to visit, more things to do, and other tourist information, you can read our West Branch route planner.

You can drive from Dubuque to West Branch in 1.5 hours. In September, plan for daily highs up to 80°F, and evening lows to 56°F. Finish your sightseeing early on the 29th (Tue) to allow enough time to travel to Mason City.

Things to do in West Branch

Historic Sites Golf Outdoors

Side Trip

Riverside Casino & Golf Resort
Highlights from your plan
Herbert Hoover National Historic Site ©
Riverside Casino & Golf Resort ©
Riverside Casino & Golf Resort

1
night
Mason City

Mason City ©
Mason City is a city in and the county seat of Cerro Gordo County, Iowa, United States. On the 30th (Wed), make a trip to Plane Crash Site of Buddy Holly, then steep yourself in history at Rock Crest - Rock Glen Historical District, then steep yourself in history at Stockman House Museum, and finally admire the striking features of Historic Park Inn Hotel.

To see traveler tips, reviews, and tourist information, you can read our Mason City journey maker app.

Getting from West Branch to Mason City by car takes about 3 hours. In September in Mason City, expect temperatures between 77°F during the day and 52°F at night. Finish up your sightseeing early on the 30th (Wed) so you can travel to Winterset.

Things to do in Mason City

Historic Sites

Side Trip

Plane Crash Site of Buddy Holly
Highlights from your plan
Stockman House Museum ©
Stockman House Museum
Historic Park Inn Hotel ©
Historic Park Inn Hotel

1
night
Winterset

Winterset ©
Winterset is a city in Madison County, Iowa, United States. On the 1st (Thu), snap pictures at Roseman Covered Bridge, then examine the collection at Iowa Quilt Museum, and then contemplate the long history of John Wayne Birthplace & Museum.

To see other places to visit, maps, traveler tips, and more tourist information, read our Winterset day trip planner.

Traveling by car from Mason City to Winterset takes 2.5 hours. Expect somewhat warmer evenings in Winterset when traveling from Mason City in September, with lows around 60°F. Finish your sightseeing early on the 1st (Thu) to allow enough time to travel back home.

Things to do in Winterset

Museums Historic Sites
Highlights from your plan
John Wayne Birthplace & Museum ©
John Wayne Birthplace & Museum
Iowa Quilt Museum ©
Iowa Quilt Museum
Roseman Covered Bridge ©
Roseman Covered Bridge

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