29 days in United States Itinerary

Created using Inspirock United States trip itinerary planner
Make it your trip
Fly
1
New York City
— 6 nights
Drive
2
Woodbury
— 4 nights
Drive
3
Washington
— 2 nights
Drive
4
Kent
— 3 nights
Drive
5
Cornwall
— 3 nights
Drive
6
Torrington
— 4 nights
Drive
7
Mystic
— 4 nights
Train to Boston Back Bay Station, Fly to Sydney

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New York City — 6 nights

Big Apple

Writer Pearl Buck once called New York City “a place apart,” and this giant urban center remains unlike any other in the world.
New York City is known for sightseeing, museums, and nightlife. Your trip includes some of its best attractions: go for a walk through Central Park, don't miss a visit to Rockefeller Center, appreciate the history behind Statue of Liberty National Monument, and enjoy breathtaking views from Top of the Rock.

To see where to stay, traveler tips, reviews, and tourist information, read New York City trip itinerary site.

Sydney, Australia to New York City is an approximately 26-hour flight. The time zone difference moving from Australian Eastern Standard Time to Eastern Standard Time is minus 15 hours. Expect a bit warmer temperatures when traveling from Sydney in September; daily highs in New York City reach 31°C and lows reach 22°C. Finish up your sightseeing early on the 4th (Wed) so you can go by car to Woodbury.
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Museums · Parks · Historic Sites · Shopping

Woodbury — 4 nights

Woodbury is a town in Litchfield County, Connecticut, United States. Get out of town with these interesting Woodbury side-trips: Wolf Conservation Center (in South Salem), Tarrywile Park & Mansion (in Danbury) and Hilltop Hanover Farm & Environmental Center (in Yorktown Heights). There's much more to do: experience rural life at Rowanwood Farm, contemplate in the serene atmosphere at Saint Anne's Church, explore the activities along Garden of Ideas, and immerse yourself in nature at Farmington Canal State Park.

For other places to visit, more things to do, traveler tips, and more tourist information, read our Woodbury sightseeing planning app.

Traveling by car from New York City to Woodbury takes 2 hours. Traveling from New York City in October, things will get little chillier in Woodbury: highs are around 20°C and lows about 8°C. Wrap up your sightseeing on the 8th (Sun) early enough to travel to Washington.
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Parks · Nature · Wildlife · Outdoors
Side Trips

Washington — 2 nights

Washington is a rural town in Litchfield County, Connecticut, in the New England region of the United States. On the 9th (Mon), relax in the rural setting at Averill Farm, then hike along Macricostas Preserve, and then identify plant and animal life at Steep Rock Preserve. On your second day here, contemplate the waterfront views at Candlewood Lake, relax in the rural setting at Green Chimneys, and then contemplate the waterfront views at Lovers Leap State Park.

Quickly create a custom-made itinerary for Washington using our trip planner.

Washington is just a stone's throw from Woodbury. In October in Washington, expect temperatures between 20°C during the day and 8°C at night. Finish your sightseeing early on the 10th (Tue) so you can travel to Kent.
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Parks · Nature · Wildlife · Outdoors
Side Trips

Kent — 3 nights

Kent is a town in Litchfield County, Connecticut, alongside the border with New York. You'll find plenty of places to visit near Kent: Mt. Ninham Fire Tower (in Carmel), Salingers Orchard Farm Market and Bakery (in Brewster) and Niese's Maple Farm (in Putnam Valley). The adventure continues: experience rural life at Shunpike Dairy, look for all kinds of wild species at Stissing Mountain Multiple Use Area, explore the fascinating underground world of Stone Church, and tour the pleasant surroundings at Cary Institute of Ecosystem Studies.

Find out how to plan Kent trip without stress by asking Inspirock to help create an itinerary.

Kent is just a stone's throw from Washington. Expect a daytime high around 22°C in October, and nighttime lows around 7°C. Finish up your sightseeing early on the 13th (Fri) so you can go by car to Cornwall.
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Parks · Outdoors · Trails · Museums
Side Trips

Cornwall — 3 nights

Cornwall is a town in Litchfield County, Connecticut, United States. Go for a jaunt from Cornwall to Ancram to see Hillrock Estate Distillery about 40 minutes away. There's still lots to do: bet on your favorite at Lime Rock Park, take in the views from West Cornwall Covered Bridge, make a trip to Beckley Furnace Industrial Monument, and stroll through Harlem Valley Rail Trail.

To find more things to do, ratings, reviews, and other tourist information, use the Cornwall trip itinerary planning site.

Cornwall is just a short distance from Kent. In October, plan for daily highs up to 20°C, and evening lows to 8°C. Wrap up your sightseeing on the 16th (Mon) early enough to travel to Torrington.
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Outdoors · Breweries & Distilleries · Trails · Parks
Side Trips

Torrington — 4 nights

Torrington is the largest city in Litchfield County, Connecticut and the Litchfield Hills region. Explore Torrington's surroundings by going to Old Drake Hill Flower Bridge (in Simsbury), Littleville Lake (in Huntington) and Keystone Arch Bridges Trail (in Chester). There's much more to do: get engrossed in the history at Hotchkiss-Fyler House Museum, contemplate the long history of Tapping Reeve House and Law School, relax in the rural setting at Flamig Farm, and delve into the lush surroundings at American Legion and Peoples State Forests.

To find more things to do, other places to visit, maps, and tourist information, go to the Torrington holiday planning tool.

Torrington is just a short distance from Cornwall. In October, plan for daily highs up to 20°C, and evening lows to 8°C. Cap off your sightseeing on the 20th (Fri) early enough to go by car to Mystic.
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Museums · Parks · Historic Sites · Nature
Side Trips

Mystic — 4 nights

A historical leading seaport, Mystic has maintained a strong respect for the past.
Explore the numerous day-trip ideas around Mystic: Point Judith Fisherman's Memorial (in Narragansett), Slater Memorial Museum (in Norwich) and Festival Farm (in Hope Valley). The adventure continues: indulge your taste buds at ShelaLara Winery Tour & Tasting, pause for some photo ops at US Submarine Veterans of WWII National Memorial East, glide peacefully along the water with East Coast Paddle Sports, and take a tour of Charles W. Morgan.

To find ratings, where to stay, maps, and tourist information, you can read our Mystic driving holiday planner.

You can drive from Torrington to Mystic in 2 hours. In October in Mystic, expect temperatures between 21°C during the day and 10°C at night. Finish up your sightseeing early on the 24th (Tue) so you can travel back home.
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Tours · Museums · Historic Sites · Outdoors
Side Trips

United States travel guide

4.6
Specialty Museums · Historic Sites · Nightlife
More than the country of car-packed streets seen in TV shows and movies, the United States of America is a complex and diverse home to over 300 million people living in a wide range of landscapes and climates. From its big-city skyscrapers to its sprawling natural parks, the country's ''melting pot'' combines many ethnic groups that share a strong sense of national identity despite their cultural differences. A country of road trips and big blue skies, the United States harbors orderly cities filled with restaurants, parks, museums, and innumerable sightseeing opportunities, as well as pristine natural areas perfect for a holiday in the great outdoors. To see as much as you can of this diverse land quickly, drive over some of the more than 6 million km (4 million mi) of highways leading through deserts, mountain peaks, fertile fields, and giant urban centers.
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