29 days in Bethlehem, Oakland & Winchester Itinerary

29 days in Bethlehem, Oakland & Winchester Itinerary

Created using Inspirock United States vacation planner

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Make it your trip
Drive
1
Bethlehem
— 11 nights
Drive
2
Oakland
— 7 nights
Drive
3
Winchester
— 9 nights
Drive to Blue Grass Airport, Fly to New York City

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Bethlehem

— 11 nights

Christmas City, USA

Listed among "Money" magazine's "Top 100 Places to Live," Bethlehem is dominated by shopping and the state's largest casino resort.
Explore the numerous day-trip ideas around Bethlehem: Longwood Gardens (in Kennett Square), Brandywine River Museum of Art (in Chadds Ford) and Jackson (Howling Woods Farm & Six Flags Great Adventure). And it doesn't end there: take in the history at Valley Forge National Historical Park, get to know the fascinating history of Hoover Mason Trestle, stroll around Grounds For Sculpture, and admire the engineering at Illick's Mill park.

To see traveler tips, reviews, ratings, and tourist information, refer to the Bethlehem driving holiday planner.

New York City to Bethlehem is an approximately 2-hour car ride. You can also take a bus; or do a combination of train and bus. Expect little chillier evenings in Bethlehem when traveling from New York City in June, with lows around 60°F. Wrap up your sightseeing on the 17th (Thu) early enough to travel to Oakland.

Things to do in Bethlehem

Parks · Museums · Theme Parks · Nature

Side Trips

Oakland

— 7 nights
Oakland is a town in the west-central part of Garrett County, Maryland. Get out of town with these interesting Oakland side-trips: Flight 93 National Memorial (in Stoystown), Jager and Friends Dog Park (in Somerset) and Flight 93 Memorial Chapel (in Stonycreek Township). There's still lots to do: immerse yourself in nature at Swallow Falls State Park, see the sights as you ascend with a climbing tour, admire the sheer force of Blackwater Falls State Park, and stroll through Great Allegheny Passage.

To see other places to visit, photos, traveler tips, and more tourist information, you can read our Oakland route builder.

Traveling by car from Bethlehem to Oakland takes 5 hours. Alternatively, you can do a combination of car and flight. When traveling from Bethlehem in June, plan for little chillier days and about the same nights in Oakland: temperatures range from 70°F by day to 56°F at night. Wrap up your sightseeing on the 25th (Fri) early enough to travel to Winchester.

Things to do in Oakland

Parks · Outdoors · Nature · Historic Sites

Side Trips

Winchester

— 9 nights
Winchester is a home rule-class city in and the county seat of Clark County, Kentucky, United States. Venture out of the city with trips to Kentucky Rock & Adventure Guides (in Pine Ridge), Berea (Union Church, Berea Pinnacles, &more) and Slade (Auxier Ridge Trail #204, Rock Bridge Trail #207, &more). There's much more to do: stroll around Red River Gorge Geological Area, examine the collection at The Great American Dollhouse Museum, steep yourself in history at White Hall State Historic Site, and relax in the rural setting at Claiborne Farm.

To find reviews, ratings, traveler tips, and other tourist information, refer to the Winchester trip itinerary planner.

Getting from Oakland to Winchester by car takes about 6 hours. Other options: do a combination of car and flight. Prepare for somewhat warmer weather when traveling from Oakland in June: high temperatures in Winchester hover around 81°F and lows are around 62°F. Cap off your sightseeing on the 4th (Sun) early enough to travel back home.

Things to do in Winchester

Parks · Historic Sites · Museums · Nature

Side Trips