8 days in Jacksonville, Pittsburgh & New York State Itinerary

8 days in Jacksonville, Pittsburgh & New York State Itinerary

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Route & dates

8 days in Jacksonville, Pittsburgh & New York State Itinerary

Start: Gainesville
Drive:  1​h 30​min
1
Jacksonville
— Few hours
flight:  6​h
2
Pittsburgh
— 3 nights
Drive:  6​h 15​min
3
Sleepy Hollow
— 1 day
Drive:  3​h 45​min
4
Lake George
— 2 nights
Drive:  3​h 15​min
5
Oswego
— 1 night
Drive:  3​h
6
Albany
— 1 night
Fly:  7​h 30​min
End: Gainesville

few
hours
Jacksonville

Jacksonville
The sprawling city of Jacksonville is not only Florida's most populous city, but also the largest city by land area in the continental United States.
To find other places to visit, reviews, more things to do, and tourist information, refer to the Jacksonville trip planner .

Gainesville to Jacksonville is an approximately 1.5-hour car ride. You can also take a bus; or do a combination of bus and train. In October, daytime highs in Jacksonville are 81°F, while nighttime lows are 62°F. You will leave for Pittsburgh on the 11th (Fri).

Things to do in Jacksonville

Outdoors Tours Parks

3
nights
Pittsburgh

Pittsburgh ©
Known primarily for its steel-related heritage and 446 bridges, Pittsburgh sits at the confluence of the Monongahela and Allegheny Rivers, which meet to form the Ohio River.
Your day-by-day itinerary now includes Fort Pitt Museum as well as Pittsburgh Zoo & PPG Aquarium. On your second day here, observe the fascinating underwater world at Pittsburgh Zoo & PPG Aquarium.

To see photos, where to stay, ratings, and more tourist information, go to the Pittsburgh trip itinerary planning website .

Do a combination of bus and flight from Jacksonville to Pittsburgh in 6 hours. Alternatively, you can do a combination of car and flight; or drive. Traveling from Jacksonville in October, expect Pittsburgh to be slightly colder, temps between 65°F and 48°F. Wrap up your sightseeing by early afternoon on the 14th (Mon) to allow time for travel to Sleepy Hollow.

Things to do in Pittsburgh

Parks Museums Zoos & Aquariums
Highlights from your plan
Pittsburgh Zoo & PPG Aquarium ©
Pittsburgh Zoo & PPG Aquarium
Fort Pitt Museum ©
Fort Pitt Museum

1
day
Sleepy Hollow

Sleepy Hollow
Sleepy Hollow is a village in the town of Mount Pleasant in Westchester County, New York. To find traveler tips, other places to visit, where to stay, and other tourist information, use the Sleepy Hollow trip maker website .

The Route module can help you plan travel from Pittsburgh to Sleepy Hollow. In October, daytime highs in Sleepy Hollow are 65°F, while nighttime lows are 49°F. You'll set off for Lake George on the 14th (Mon).

Things to do in Sleepy Hollow

Parks Historic Sites Wildlife

2
nights
Lake George

Lake George ©
A playground for America’s wealthy families, Lake George was nicknamed "Queen of the American Lakes." While these families often stayed in private country houses, a tourism industry built up around them in the early 20th century facilitated by two YMCAs.
You've now added The Fort William Henry Museum & Restoration to your itinerary. On the 15th (Tue), get engrossed in the history at The Fort William Henry Museum & Restoration, do a tasting at Adirondack Winery, and then learn about winemaking at Adirondack Winery.

For more things to do, traveler tips, where to stay, and other tourist information, go to the Lake George holiday planner.

You can drive from Sleepy Hollow to Lake George in 3.5 hours. Traveling from Sleepy Hollow in October, you can expect nighttime temperatures to be slightly colder in Lake George, with lows of 40°F. Wrap up your sightseeing by early afternoon on the 16th (Wed) to allow enough time to travel to Oswego.

Things to do in Lake George

Museums Wineries

Side Trip

Adirondack Winery Bolton Landing Tasting Room
Highlights from your plan
Adirondack Winery ©
Adirondack Winery

1
night
Oswego

Oswego ©
Oswego is a city in Oswego County, New York, United States. Kick off your visit on the 16th (Wed): brush up on your military savvy at Fort Ontario State Historic Site, then relax in the rural setting at Ontario Orchards, and then relax in the rural setting at Wager's Country Apple Farm. On the 17th (Thu), you'll have a packed day of sightseeing: get to know the resident critters at Rosamond Gifford Zoo.

To see more things to do, other places to visit, maps, and more tourist information, read our Oswego itinerary builder website .

Traveling by car from Lake George to Oswego takes 3.5 hours. October in Oswego sees daily highs of 62°F and lows of 45°F at night. On the 17th (Thu), wrap the sightseeing up by early afternoon so you can travel to Albany.

Things to do in Oswego

Parks Museums Zoos & Aquariums

Side Trips

Wager's Country Apple Farm, Rosamond Gifford Zoo
Highlights from your plan
Rosamond Gifford Zoo ©
Rosamond Gifford Zoo
Fort Ontario State Historic Site ©
Fort Ontario State Historic Site
Ontario Orchards ©
Ontario Orchards

1
night
Albany

Albany
Albany is the capital of the U.S. On the 18th (Fri), sample the fine beverages at The Albany Distilling Company.

For traveler tips, other places to visit, more things to do, and other tourist information, read our Albany tour website .

Drive from Oswego to Albany in 3 hours. October in Albany sees daily highs of 63°F and lows of 44°F at night. You will have some time to spend on the 18th (Fri) before leaving for home.

Things to do in Albany

Breweries & Distilleries

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