29 days in Bethlehem, Oakland & Winchester Itinerary

29 days in Bethlehem, Oakland & Winchester Itinerary

Created using Inspirock United States vacation planner
©
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

S M T W T F S
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
1
2
3
4
5
6
7
8
9
10

Bethlehem — 11 nights

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), Jackson (Howling Woods Farm & Six Flags Great Adventure) and Brandywine River Museum of Art (in Chadds Ford). And it doesn't end there: witness the site of a historic battle at Valley Forge National Historical Park, get to know the fascinating history of Hoover Mason Trestle, view the masterpieces at SteelStacks, and walk around Illick's Mill park.

To find reviews, ratings, other places to visit, and more tourist information, you can read our Bethlehem trip maker tool.

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. Traveling from New York City in June, Bethlehem is little chillier at night with lows of 60°F. Finish your sightseeing early on the 17th (Thu) so you can travel to Oakland.
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 Memorial Chapel (in Stonycreek Township), Jager and Friends Dog Park (in Somerset) and Flight 93 National Memorial (in Stoystown). There's still lots to do: contemplate the long history of Fallingwater, admire the sheer force of Blackwater Falls State Park, examine the collection at Garrett County Historical Museum, 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.
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 Slade (Auxier Ridge Trail #204, Rock Bridge Trail #207, &more), Kentucky Rock & Adventure Guides (in Pine Ridge) and Berea (Union Church, Berea Pinnacles, &more). There's still lots to do: walk around Red River Gorge Geological Area, look for gifts at Dirty South Pottery, delve into the lush surroundings at Daniel Boone National Forest, and get engrossed in the history at Bluegrass Heritage Museum.

For more things to do, maps, photos, and more tourist information, refer to the Winchester road trip planning website.

Traveling by car from Oakland to Winchester takes 6 hours. Alternatively, you can do a combination of car and flight. Traveling from Oakland in June, things will get somewhat warmer in Winchester: highs are around 81°F and lows about 62°F. Finish your sightseeing early on the 4th (Sun) to allow enough time to travel back home.
Parks · Historic Sites · Museums · Nature
Side Trips