22 days in United States Itinerary

22 days in United States Itinerary

Created using Inspirock United States trip planner

©
Plan created by another user. Make it yours
Drive
1
Port Jervis
— 1 night
Drive
2
Warwick
— 3 nights
Drive
3
Cragsmoor
— 1 night
Drive
4
New Paltz
— 2 nights
Drive
5
Kingston
— 3 nights
Drive
6
Manchester
— 3 nights
Drive
7
Windsor
— 2 nights
Drive
8
New London
— 1 night
Drive
9
Wilton
— Few hours
Drive
10
Tarrytown
— Few hours
Drive
11
Monroe
— 1 night
Drive
12
Stony Point
— 1 night
Drive
13
Cold Spring
— 1 night
Drive
14
New Windsor
— 1 night
Drive

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

1
night
Port Jervis

Port Jervis is a city located at the confluence of the Neversink and the Delaware rivers in western Orange County, New York, north of the Delaware Water Gap. Your day by day itinerary now includes Tri-States Rock. Start off your visit on the 2nd (Fri): pause for some photo ops at Tri-States Rock and then cruise along Hawk's Nest Highway.

For ratings, reviews, other places to visit, and other tourist information, refer to the Port Jervis vacation builder website.

Annapolis to Port Jervis is an approximately 4.5-hour car ride. You can also drive; or do a combination of car and flight. Traveling from Annapolis in October, expect a bit cooler with lows of 43°F in Port Jervis. On the 3rd (Sat), wrap the sightseeing up by early afternoon so you can travel to Warwick.

Things to do in Port Jervis

Scenic Drive · Outdoors
Highlights from your trip
Hawk's Nest Highway ©
Scenic Drive
Hawk's Nest Highway
4.8
Tri-States Rock ©
Monument
Tri-States Rock
3.9

3
nights
Warwick

Located in one of the Northeast’s prime apple-growing regions and home to the annual Applefest celebration, Warwick blends a series of villages, each with its own main street.
Warwick is known for wineries, nightlife, and shopping. Your plan includes some of its best attractions: relax in the rural setting at Masker Orchards.

For ratings, traveler tips, and tourist information, use the Warwick road trip app.

You can drive from Port Jervis to Warwick in an hour. Another option is to drive. In October in Warwick, expect temperatures between 66°F during the day and 43°F at night. Wrap up your sightseeing by early afternoon on the 6th (Tue) to allow time for travel to Cragsmoor.
Highlights from your trip

1
night
Cragsmoor

Cragsmoor is a hamlet (and census-designated place) in Ulster County, New York, United States. Sam's Point Preserve has been added to your itinerary. On the 6th (Tue), look for all kinds of wild species at Sam's Point Preserve, then admire the sheer force of Ice Caves and Verkeerderkill Falls Trail Hike, and then take in the architecture and atmosphere at Cragsmoor Stone Church.

For maps, where to stay, photos, and other tourist information, you can read our Cragsmoor trip itinerary maker site.

Getting from Warwick to Cragsmoor by car takes about an hour. Other options: drive. In October, plan for daily highs up to 66°F, and evening lows to 43°F. Finish your sightseeing early on the 7th (Wed) to allow enough time to travel to New Paltz.

Things to do in Cragsmoor

Parks · Wildlife · Historic Sites · Nature
Highlights from your trip

2
nights
New Paltz

New Paltz is a town in Ulster County, New York, United States. Kick off your visit on the 7th (Wed): experience rural life at Jenkins Lueken Orchards, look for all kinds of wild species at Nyquist-Harcourt Wildlife Sanctuary, and then don't miss a visit to The Testimonial Gateway. Here are some ideas for day two: appreciate the extensive heritage of Widow Jane Mine, relax in the rural setting at Sprout Creek Farm, and then take in the spiritual surroundings of Calvary Chapel of the Hudson Valley.

To find maps, traveler tips, more things to do, and more tourist information, go to the New Paltz trip planner.

Drive from Cragsmoor to New Paltz in an hour. Alternatively, you can drive. In October in New Paltz, expect temperatures between 67°F during the day and 43°F at night. Wrap up your sightseeing on the 9th (Fri) early enough to drive to Kingston.

Things to do in New Paltz

Historic Sites · Wildlife · Parks

Side Trips

Highlights from your trip
Widow Jane Mine ©
Historic Walking Area
Widow Jane Mine
4.8

3
nights
Kingston

Kingston is a city in and the county seat of Ulster County, New York, United States. You've now added Hudson River Maritime Museum to your itinerary. Step off the beaten path and head to Historic Huguenot Street and The Clermont Mansion. Your inner history buff will appreciate Thomas Cole National Historic Site and Old Dutch Church. Step out of Kingston with an excursion to Berkshire Mountain Distillers in Sheffield--about 1h 10 min away. Next up on the itinerary: hike along The Wallkill Valley Rail Trail, take in the views from Walkway Over the Hudson State Historic Park, stroll around Forsyth Park, and see the interesting displays at Kingston Uptown Historic District.

To see other places to visit, ratings, where to stay, and more tourist information, you can read our Kingston online journey planner.

Kingston is just a short distance from New Paltz. October in Kingston sees daily highs of 67°F and lows of 43°F at night. Finish your sightseeing early on the 12th (Mon) to allow enough time to travel to Manchester.

Things to do in Kingston

Historic Sites · Museums · Parks · Trails

Side Trips

Highlights from your trip

3
nights
Manchester

Manchester is a town in, and one of two shire towns (county seats) of, Bennington County, Vermont, United States. You'll explore the less-touristy side of things at Lye Brook Falls and Dana L. Thompson Memorial Park. Take a break from the city and head to Equinox Preservation Trust and Molly Stark Trail. Venture out of the city with trips to Papermill Village Bridge (in North Bennington) and Bennington (Fiddlehead at Four Corners & Silk Road Covered Bridge). There's much more to do: take in the exciting artwork at Southern Vermont Arts Center, take in the views from Bridge at the Green, relax in the rural setting at North Meadow Farm, and see the interesting displays at The American Museum of Fly Fishing.

To find where to stay, ratings, other places to visit, and more tourist information, use the Manchester trip planner.

You can drive from Kingston to Manchester in 2.5 hours. Another option is to drive. When traveling from Kingston in October, plan for a bit cooler days and about the same nights in Manchester: temperatures range from 62°F by day to 41°F at night. Finish your sightseeing early on the 15th (Thu) so you can drive to Windsor.

Things to do in Manchester

Parks · Museums · Wildlife · Shopping

Side Trips

Highlights from your trip

2
nights
Windsor

Windsor is a town in Windsor County, Vermont, United States. Start off your visit on the 15th (Thu): admire the majestic nature at Chesterfield Gorge State Park, take in the views from West Dummerston Covered Bridge, and then relax in the rural setting at Green Mountain Orchards. On the 16th (Fri), you'll have a packed day of sightseeing: admire the natural beauty at Cider Hill Gardens, then stop by Vermont Alpaca Store & Living the Dream Alpaca Farm, then relax in the rural setting at Mac's Maple, and finally stroll around Paradise Park.

To see where to stay, reviews, and tourist information, read our Windsor tour itinerary planner.

Traveling by car from Manchester to Windsor takes 1.5 hours. Alternatively, you can drive. Expect a daytime high around 62°F in October, and nighttime lows around 40°F. Finish your sightseeing early on the 17th (Sat) to allow enough time to travel to New London.

Things to do in Windsor

Parks · Nature · Shopping

Side Trips

Highlights from your trip

1
night
New London

New London is a town in Merrimack County, New Hampshire, United States. Your day by day itinerary now includes Mount Kearsarge. Kick off your visit on the 17th (Sat): take your sightseeing to a higher altitude at Mount Kearsarge, then admire the majestic nature at Rollins State Park, and then admire the majestic nature at Winslow State Park.

For ratings, maps, traveler tips, and more tourist information, read New London road trip planning tool.

Traveling by car from Windsor to New London takes an hour. Alternatively, you can drive. In October, plan for daily highs up to 62°F, and evening lows to 40°F. Finish up your sightseeing early on the 18th (Sun) so you can travel to Wilton.

Things to do in New London

Nature · Parks · Trails · Outdoors

Side Trips

Highlights from your trip
Mount Kearsarge ©
Must see
Mount Kearsarge
4.9
Winslow State Park ©
State Park
Winslow State Park
4.9
Rollins State Park ©
State Park
Rollins State Park
4.7

few
hours
Wilton

Wilton is a town in Fairfield County in southwestern Connecticut in the United States. Before you visit Wilton, use our trip planner to discover what you can do and see there.

Traveling by car from New London to Wilton takes 4 hours. Alternatively, you can drive. In October, daytime highs in Wilton are 65°F, while nighttime lows are 44°F. On the 18th (Sun), you'll travel to Tarrytown.

Things to do in Wilton

Parks · Museums · Historic Sites · Wildlife

few
hours
Tarrytown

Tarrytown is a village in the town of Greenburgh in Westchester County, New York, United States. To find other places to visit, more things to do, traveler tips, and tourist information, read Tarrytown trip builder app.

You can drive from Wilton to Tarrytown in an hour. Alternatively, you can drive. Expect a daytime high around 65°F in October, and nighttime lows around 49°F. You will leave for Monroe on the 18th (Sun).

Things to do in Tarrytown

Parks · Outdoors · Museums · Nightlife

1
night
Monroe

On the 18th (Sun), relax in the rural setting at Bellvale Farms Creamery and then take in the dramatic scenery at Fitzgerald Falls.

To find other places to visit, reviews, and other tourist information, use the Monroe trip tool.

You can drive from Tarrytown to Monroe in an hour. Alternatively, you can drive. In October, daytime highs in Monroe are 64°F, while nighttime lows are 46°F. Finish up your sightseeing early on the 19th (Mon) so you can travel to Stony Point.

Things to do in Monroe

Trails · Wildlife · Outdoors · Nature

Side Trip

Highlights from your trip
Fitzgerald Falls ©
Waterfall
Fitzgerald Falls
4.0

1
night
Stony Point

Stony Point is a triangle-shaped town in Rockland County, New York, United States. On the 19th (Mon), take in the architecture and atmosphere at Church of the Immaculate Heart of Mary, then admire the majestic nature at High Tor State Park, then relax in the rural setting at Faraway Farm Alpacas, and finally explore the striking landscape of Croton Gorge Park.

To see where to stay, photos, maps, and other tourist information, go to the Stony Point travel route planning tool.

Stony Point is just a stone's throw from Monroe. In October in Stony Point, expect temperatures between 65°F during the day and 49°F at night. Wrap up your sightseeing on the 20th (Tue) to allow time to travel to Cold Spring.

Things to do in Stony Point

Nature · Parks · Historic Sites

Side Trips

Highlights from your trip
High Tor State Park ©
State Park
High Tor State Park
4.3
Croton Gorge Park ©
National Park
Croton Gorge Park
4.8

1
night
Cold Spring

Cold Spring is a village in the town of Philipstown in Putnam County, New York, United States. Your day by day itinerary now includes West Point Foundry Preserve, Bannerman Castle and Breakneck Ridge Loop. On the 20th (Tue), explore the historical opulence of Bannerman Castle, contemplate the long history of West Point Foundry Preserve, take in the awesome beauty at Breakneck Ridge Loop, then take in the awesome beauty at Bull Hill (Mt.Taurus), then look for all kinds of wild species at Magazzino Italian Art, and finally appreciate the history behind Statue of General Tadeusz Kosciuszko.

To see other places to visit, photos, and more tourist information, refer to the Cold Spring tour website.

Cold Spring is just a short distance from Stony Point. In October, daily temperatures in Cold Spring can reach 64°F, while at night they dip to 46°F. Wrap up your sightseeing on the 21st (Wed) early enough to travel to New Windsor.

Things to do in Cold Spring

Parks · Historic Sites · Trails · Outdoors

Side Trip

Highlights from your trip
Bannerman Castle ©
Must see
Bannerman Castle
4.6
Breakneck Ridge Loop
Mountain
Breakneck Ridge Loop
4.0

1
night
New Windsor

New Windsor is a town in Orange County, New York, United States. On the 21st (Wed), brush up on your military savvy at New Windsor Cantonment State Historic Site, learn about all things military at National Purple Heart Hall Of Honor, and then identify plant and animal life at Orange County Arboretum. On the 22nd (Thu), you'll have a packed day of sightseeing: immerse yourself in nature at Schunnemunk State Park, enjoy the sand and surf at Kowawese Unique Area at Plum Point, and then explore the landscape on two wheels at Dutchess Rail Trail.

To find where to stay, more things to do, ratings, and other tourist information, read our New Windsor visit planner.

New Windsor is very close to Cold Spring. In October, daily temperatures in New Windsor can reach 64°F, while at night they dip to 46°F. Finish your sightseeing early on the 22nd (Thu) so you can travel back home.

Things to do in New Windsor

Parks · Museums · Wildlife · Outdoors

Side Trips

Highlights from your trip
Orange County Arboretum ©
Wildlife Area
Orange County Arboretum
4.5
Dutchess Rail Trail ©
Biking Trail
Dutchess Rail Trail
5.0

Similar trips

24 days in Vermont BY A USER FROM UKRAINE March, popular sights Preferences: March Attraction style: Popular sights Pace: Medium 30 days in United States BY A USER FROM UNITED STATES April, culture, outdoors, beaches, historic sites, museums, popular & hidden gems Preferences: April, culture, outdoors, beaches, historic sites, museums Attraction style: Popular & hidden gems Pace: Medium 28 days in New Hampshire BY A USER FROM UNITED STATES March, popular sights Preferences: March Attraction style: Popular sights Pace: Medium 31 days in New Hampshire BY A USER FROM UNITED STATES October, popular sights Preferences: October Attraction style: Popular sights Pace: Medium 32 days in Vermont BY A USER FROM UNITED STATES August, popular sights Preferences: August Attraction style: Popular sights Pace: Medium 20 days in East Coast of USA & Vermont BY A USER FROM AUSTRALIA July, kids, popular sights Preferences: July, kids Attraction style: Popular sights Pace: Medium 8 days in Vermont BY A USER FROM CANADA March, teens, culture, historic sites, museums, shopping, hidden gems Preferences: March, teens, culture, historic sites, museums, shopping Attraction style: Hidden gems Pace: Medium 5 days in Vermont BY A USER FROM UNITED STATES February, relaxing, romantic, shopping, popular & hidden gems Preferences: February, relaxing, romantic, shopping Attraction style: Popular & hidden gems Pace: Medium 5 days in Vermont BY A USER FROM UNITED STATES February, culture, relaxing, romantic, popular & hidden gems Preferences: February, culture, relaxing, romantic Attraction style: Popular & hidden gems Pace: Medium 7 days in New Hampshire BY A USER FROM UNITED STATES April, relaxing, romantic, beaches, popular & hidden gems Preferences: April, relaxing, romantic, beaches Attraction style: Popular & hidden gems Pace: Medium
See more trips