52 days in United States & Canada Itinerary

52 days in United States & Canada Itinerary

Created using Inspirock trip planner

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Route & dates

Start: Perth, Australia
Fly:  30 h
1
Boston, United States
— 1 night
Drive + Ferry:  2 h 30 min
2
Nantucket, United States
— 2 nights
Drive:  2 h 30 min
3
Vineyard Haven, United States
— 1 night
Drive:  2 h 15 min
4
Dennis, United States
— 2 nights
Drive:  3 h 15 min
5
Cromwell, United States
— 1 night
Drive:  1 h
6
Litchfield, United States
— 1 night
Drive:  2 h 15 min
7
Saratoga Springs, United States
— 1 night
Drive:  3 h 15 min
8
Stowe, United States
— 1 night
Drive:  2 h 30 min
9
Lake Placid, United States
— 1 night
Drive:  2 h 45 min
10
Pulaski, United States
— 1 night
Drive:  45 min
11
Syracuse, United States
— 1 night
Drive:  1 h 45 min
12
Watkins Glen, United States
— 1 night
Drive:  1 h 45 min
13
Rochester, United States
— 1 night
Drive:  1 h 45 min
14
Niagara Falls, United States
— 1 night
Drive:  15 min
15
Niagara Falls, Canada
— 1 night
Drive:  1 h 30 min
16
Toronto, Canada
— 3 nights
Fly:  2 h 45 min
17
Kingston, Canada
— 2 nights
Drive:  2 h 15 min
18
Ottawa, Canada
— 3 nights
Train:  2 h 15 min
19
Montreal, Canada
— 2 nights
Fly + Drive:  8 h
20
Bennington, United States
— 3 nights
Drive:  45 min
21
Peru, United States
— 1 night
Drive:  30 min
22
Arlington, United States
— 1 night
Drive:  4 h
23
North Conway, United States
— 4 nights
Drive:  1 h 30 min
24
Gilford, United States
— 2 nights
+2
Drive + Fly + Drive:  8 h 45 min
25
Bar Harbor, United States
— 2 nights
Drive:  4 h 15 min
26
Portsmouth, United States
— 3 nights
Drive:  1 h 15 min
27
Boston, United States
— 3 nights
Fly:  4 h
28
Chicago, United States
— 3 nights
Fly:  29 h
End: Perth, Australia

1
night
Boston, United States

Boston
Rich in museums, restaurants, shops, and historical sites, Boston attracts over 16 million visitors each year. New England's largest and most influential city, Boston ranks among the world's major centers of education and culture.
To find reviews, maps, traveler tips, and tourist information, read Boston trip planner.

Perth, Australia to Boston is an approximately 31- hour flight. You can also do a combination of flight and train; or do a combination of flight and ferry. The time zone difference moving from Australian Western Standard Time to Eastern Standard Time is minus 13 hours. Plan for somewhat warmer temperatures traveling from Perth in September, with highs in Boston at 28°C and lows at 17°C. On the 24th (Sat), you're off to Nantucket.

Things to do in Boston

Parks Outdoors Museums

2
nights
Nantucket, United States

Nantucket ©
Nantucket is an island about 30mi by ferry south from Cape Cod, in the American state of Massachusetts. Kick off your visit on the 24th (Sat): examine the collection at Nantucket Lightship Basket Museum, then stop by The Hub, then examine the collection at Whaling Museum, and finally stroll through Jetties Beach. On the 25th (Sun), you'll have a packed day of sightseeing: enjoy the sea views from Sankaty Head Lighthouse, then take in the architecture and atmosphere at St Paul's Episcopal Church, then enjoy the sea views from Brant Point Lighthouse, and finally tour the pleasant surroundings at Madaket Beach.

Before you visit Nantucket, use our trip planner to discover what you can do and see there.

You can do a combination of car and ferry from Boston to Nantucket in 2.5 hours. Alternatively, you can fly; or do a combination of bus and flight. In September in Nantucket, expect temperatures between 25°C during the day and 17°C at night. Wrap up your sightseeing on the 26th (Mon) early enough to drive to Vineyard Haven.

Things to do in Nantucket

Beaches Outdoors Parks
Highlights from your plan
Jetties Beach ©
Jetties Beach
Whaling Museum ©
Whaling Museum
Sankaty Head Lighthouse ©
Sankaty Head Lighthouse

1
night
Vineyard Haven, United States

Vineyard Haven ©
Vineyard Haven is a community within the town of Tisbury on Martha's Vineyard in Dukes County, Massachusetts, United States. On the 26th (Mon), take a stroll through Martha's Vineyard Camp meeting Association (MVCMA), visit a coastal fixture at Edgartown Lighthouse, then enjoy the sand and surf at Katama Beach/ South Beach, and finally contemplate the long history of Aquinnah Cliffs.

To see traveler tips, ratings, photos, and more tourist information, read Vineyard Haven trip planning tool.

You can drive from Nantucket to Vineyard Haven in 2.5 hours. Expect a bit cooler evenings in Vineyard Haven when traveling from Nantucket in September, with lows around 14°C. Finish your sightseeing early on the 27th (Tue) so you can drive to Dennis.

Things to do in Vineyard Haven

Parks Historic Sites Beaches

Side Trips

Edgartown, Aquinnah Cliffs, Martha's Vineyard Camp meeting Association (MVCMA)
Highlights from your plan
Katama Beach/ South Beach ©
Katama Beach/ South Beach
Edgartown Lighthouse ©
Edgartown Lighthouse

2
nights
Dennis, United States

Dennis ©
Dennis is a town in Barnstable County, Massachusetts, United States, located near the center of Cape Cod. On the 27th (Tue), get lost in a book at Provincetown Library, make a trip to Commercial Street, then appreciate the history behind Pilgrim Monument & Provincetown Museum, and finally tour the pleasant surroundings at Corporation Beach. Get ready for a full day of sightseeing on the next day: examine the collection at Heritage Museums & Gardens, then take an in-depth tour of Plimoth Plantation, then pause for some photo ops at Plymouth Rock, and finally make a trip to Mayflower II.

To see more things to do, reviews, photos, and tourist information, read Dennis online day trip planner.

Traveling by car from Vineyard Haven to Dennis takes 2.5 hours. In September in Dennis, expect temperatures between 26°C during the day and 16°C at night. Finish your sightseeing early on the 29th (Thu) so you can travel to Cromwell.

Things to do in Dennis

Museums Beaches Outdoors

Side Trips

Plymouth, Provincetown, Heritage Museums & Gardens
Highlights from your plan
Pilgrim Monument & Provincetown Museum ©
Pilgrim Monument & Provincetown Museum
Heritage Museums & Gardens ©
Heritage Museums & Gardens
Plimoth Plantation ©
Plimoth Plantation

1
night
Cromwell, United States

Cromwell ©
Cromwell is a town in Middlesex County, Connecticut, United States located in the middle of the state. Start off your visit on the 29th (Thu): see the interesting displays at Dinosaur State Park, learn about winemaking at Gouveia Vineyards, then explore the world behind art at New Britain Museum of American Art, and finally hike along Cotton Hollow Preserve.

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

Traveling by car from Dennis to Cromwell takes 3 hours. In September, daytime highs in Cromwell are 30°C, while nighttime lows are 16°C. Wrap up your sightseeing on the 30th (Fri) early enough to travel to Litchfield.

Things to do in Cromwell

Museums Wineries Trails

Side Trips

Dinosaur State Park, Cotton Hollow Preserve, Gouveia Vineyards, New Britain Museum of American Art
Highlights from your plan
New Britain Museum of American Art ©
New Britain Museum of American Art
Gouveia Vineyards ©
Gouveia Vineyards
Dinosaur State Park ©
Dinosaur State Park

1
night
Litchfield, United States

Litchfield ©
Litchfield is a town in and former county seat of Litchfield County, Connecticut, United States. Kick off your visit on the 30th (Fri): look for gifts at Thorncrest Farm and Milk House Chocolate, admire the majestic nature at Kent Falls State Park, then identify plant and animal life at White Memorial Conservation Center, and finally do a tasting at Haight-Brown Vineyard.

To find where to stay, ratings, other places to visit, and more tourist information, read Litchfield vacation maker.

You can drive from Cromwell to Litchfield in an hour. September in Litchfield sees daily highs of 27°C and lows of 14°C at night. Cap off your sightseeing on the 1st (Sat) early enough to travel to Saratoga Springs.

Things to do in Litchfield

Parks Wineries Wildlife

Side Trips

Thorncrest Farm and Milk House Chocolate, Kent Falls State Park
Highlights from your plan
Kent Falls State Park ©
Kent Falls State Park
White Memorial Conservation Center ©
White Memorial Conservation Center
Thorncrest Farm and Milk House Chocolate ©
Thorncrest Farm and Milk House Chocolate

1
night
Saratoga Springs, United States

Saratoga Springs ©
Named for the restorative mineral springs in the area, Saratoga Springs began its life as a resort town.
Start off your visit on the 1st (Sat): stop by Impressions of Saratoga, then try to win big at Saratoga Race Course, then immerse yourself in nature at Saratoga Spa State Park, and finally stroll around Congress Park.

To find ratings, more things to do, where to stay, and tourist information, read Saratoga Springs itinerary planner.

Getting from Litchfield to Saratoga Springs by car takes about 2.5 hours. In October, daytime highs in Saratoga Springs are 19°C, while nighttime lows are 9°C. Finish your sightseeing early on the 2nd (Sun) to allow enough time to drive to Stowe.

Things to do in Saratoga Springs

Parks Casinos Fun & Games
Highlights from your plan
Saratoga Spa State Park ©
Saratoga Spa State Park
Saratoga Race Course ©
Saratoga Race Course
Impressions of Saratoga ©
Impressions of Saratoga

1
night
Stowe, United States

Stowe ©
Stowe bustles in winter when skiers and snowboarders flock here to challenge themselves on the long, steep trails careening down Vermont's tallest peak, Mt.
Kick off your visit on the 2nd (Sun): hit the slopes at Stowe Mountain Resort, then hike along Stowe Recreation Path, then take your sightseeing to a higher altitude at Mount Mansfield State Forest, and finally view the masterpieces at Remarkable Things at Stowe Craft.

To see ratings, reviews, photos, and other tourist information, you can read our Stowe trip planner.

You can drive from Saratoga Springs to Stowe in 3.5 hours. Another option is to do a combination of train, car, and ferry. Traveling from Saratoga Springs in October, Stowe is a bit cooler at night with lows of 4°C. Finish your sightseeing early on the 3rd (Mon) to allow enough time to drive to Lake Placid.

Things to do in Stowe

Parks Outdoors Winter Sports
Highlights from your plan
Stowe Recreation Path ©
Stowe Recreation Path
Mount Mansfield State Forest ©
Mount Mansfield State Forest
Remarkable Things at Stowe Craft ©
Remarkable Things at Stowe Craft

1
night
Lake Placid, United States

Lake Placid ©
Lake Placid is a village in the Adirondack Mountains in Essex County, New York, United States. On the 3rd (Mon), tour the pleasant surroundings at Whiteface Mountain, then stop by Saratoga Olive Oil, then contemplate the waterfront views at Mirror Lake, and finally take some stellar pictures from Olympic Ski Jump Complex.

To find more things to do, maps, other places to visit, and tourist information, you can read our Lake Placid online route planner.

Traveling by car from Stowe to Lake Placid takes 2.5 hours. Alternatively, you can do a combination of bus, ferry, and car. Traveling from Stowe in October, Lake Placid is little chillier at night with lows of 1°C. Wrap up your sightseeing on the 4th (Tue) early enough to travel to Pulaski.

Things to do in Lake Placid

Nature Parks Winter Sports

Side Trip

Whiteface Mountain
Highlights from your plan
Mirror Lake ©
Mirror Lake
Whiteface Mountain ©
Whiteface Mountain
Olympic Ski Jump Complex ©
Olympic Ski Jump Complex

1
night
Pulaski, United States

Pulaski ©
Pulaski is a village in Oswego County, New York, United States. On the 4th (Tue), admire the sheer force of Salmon River Falls, then immerse yourself in nature at Selkirk Shores State Park, and then contemplate the waterfront views at Salmon River.

To find more things to do, photos, and other tourist information, you can read our Pulaski online itinerary builder.

Drive from Lake Placid to Pulaski in 3.5 hours. Traveling from Lake Placid in October, you can expect nighttime temperatures to be a bit warmer in Pulaski, with lows of 8°C. Finish up your sightseeing early on the 5th (Wed) so you can go by car to Syracuse.

Things to do in Pulaski

Nature Parks

Side Trip

Salmon River Falls
Highlights from your plan
Salmon River Falls ©
Salmon River Falls
Selkirk Shores State Park ©
Selkirk Shores State Park

1
night
Syracuse, United States

Syracuse ©
Syracuse is a city in, and the county seat of, Onondaga County, New York, in the United States. On the 5th (Wed), admire the landmark architecture of Clinton Square, learn about wildlife with up-close encounters at Rosamond Gifford Zoo, and then shop like a local with Destiny USA.

To find more things to do, other places to visit, and tourist information, read our Syracuse trip app.

Getting from Pulaski to Syracuse by car takes about an hour. In October, daily temperatures in Syracuse can reach 20°C, while at night they dip to 8°C. Finish your sightseeing early on the 6th (Thu) so you can drive to Watkins Glen.

Things to do in Syracuse

Shopping Zoos & Aquariums Parks
Highlights from your plan
Destiny USA ©
Destiny USA
Rosamond Gifford Zoo ©
Rosamond Gifford Zoo
Clinton Square ©
Clinton Square

1
night
Watkins Glen, United States

Watkins Glen ©
Watkins Glen is a village in Schuyler County, New York, United States. Kick off your visit on the 6th (Thu): cruise along Seneca Lake Wine Trail and then immerse yourself in nature at Watkins Glen State Park.

To see photos, ratings, where to stay, and more tourist information, read Watkins Glen trip itinerary planning tool.

You can drive from Syracuse to Watkins Glen in 2 hours. Alternatively, you can take a bus. In October, daytime highs in Watkins Glen are 20°C, while nighttime lows are 6°C. Wrap up your sightseeing on the 7th (Fri) early enough to drive to Rochester.

Things to do in Watkins Glen

Scenic Drive Outdoors Nature
Highlights from your plan
Seneca Lake Wine Trail ©
Seneca Lake Wine Trail
Watkins Glen State Park ©
Watkins Glen State Park

1
night
Rochester, United States

Rochester ©
Blending big-city culture with small-town charm, Rochester sits on the southern shore of Lake Ontario.
Start off your visit on the 7th (Fri): admire nature's wide array of creatures at Seneca Park Zoo, have fun and explore at The Strong National Museum of Play, and then explore the different monuments and memorials at Mount Hope Cemetery.

To see where to stay, photos, maps, and tourist information, refer to the Rochester road trip planning website.

You can drive from Watkins Glen to Rochester in 2 hours. Another option is to take a bus. Expect a daytime high around 20°C in October, and nighttime lows around 8°C. Finish up your sightseeing early on the 8th (Sat) so you can go by car to Niagara Falls.

Things to do in Rochester

Zoos & Aquariums Museums Childrens Museums
Highlights from your plan
Seneca Park Zoo ©
Seneca Park Zoo
The Strong National Museum of Play ©
The Strong National Museum of Play
Mount Hope Cemetery ©
Mount Hope Cemetery

1
night
Niagara Falls, United States

Niagara Falls ©
The city of Niagara Falls houses the U.S.
Kick off your visit on the 8th (Sat): admire the striking features of Frank Lloyd Wright's Martin House, take in the architecture and atmosphere at St. Mary of the Cataract R. C. Parish, and then Head underground at Cave of the Winds.

To see more things to do, ratings, photos, and more tourist information, read our Niagara Falls trip itinerary planner.

Getting from Rochester to Niagara Falls by car takes about 2 hours. Other options: take a train; or take a bus. In October in Niagara Falls, expect temperatures between 20°C during the day and 9°C at night. Wrap up your sightseeing on the 9th (Sun) early enough to drive to Niagara Falls.

Things to do in Niagara Falls

Historic Sites Nature Parks

Side Trip

Frank Lloyd Wright's Martin House
Highlights from your plan
Frank Lloyd Wright's Martin House ©
Frank Lloyd Wright's Martin House
Cave of the Winds ©
Cave of the Winds
St. Mary of the Cataract R. C. Parish ©
St. Mary of the Cataract R. C. Parish

1
night
Niagara Falls, Canada

Niagara Falls ©
Indisputably one of the world's most impressive natural sights, Niagara Falls straddle the United States/Canada border, marking the spot at which a thundering river plunges over a major escarpment.
On the 9th (Sun), enjoy breathtaking views from Skylon Tower, don't miss a visit to Journey Behind the Falls, then take in the dramatic scenery at Niagara Falls Canada, and finally have some family-friendly fun at BATL - The Backyard Axe Throwing League.

Before you visit Niagara Falls, use our trip planner to discover what you can do and see there.

Niagara Falls is very close to Niagara Falls. In October in Niagara Falls, expect temperatures between 20°C during the day and 9°C at night. Cap off your sightseeing on the 10th (Mon) early enough to go by car to Toronto.

Things to do in Niagara Falls

Nature Parks Fun & Games
Highlights from your plan
Niagara Falls Canada ©
Niagara Falls Canada
Journey Behind the Falls ©
Journey Behind the Falls
Skylon Tower ©
Skylon Tower

3
nights
Toronto, Canada

Toronto
Possibly the world's most diverse city, Toronto houses over 80 ethnic communities speaking nearly 150 different languages or dialects.
Toronto is known for zoos & aquariums, museums, and shopping. Your plan includes some of its best attractions: enjoy breathtaking views from CN Tower, indulge your thirst for a good beer at Steam Whistle Brewery, stroll around Toronto Island Park, and explore the historical opulence of Casa Loma.

To see ratings, other places to visit, reviews, and other tourist information, use the Toronto road trip planning website.

Getting from Niagara Falls to Toronto by car takes about 1.5 hours. Other options: take a train; or take a bus. In October, plan for daily highs up to 18°C, and evening lows to 9°C. Finish your sightseeing early on the 13th (Thu) so you can travel to Kingston.

Things to do in Toronto

Museums Historic Sites Parks
Highlights from your plan
CN Tower
CN Tower
Casa Loma ©
Casa Loma
The Distillery District ©
The Distillery District

2
nights
Kingston, Canada

Kingston ©
Called the "Limestone City" because it contains many white-stone buildings, Kingston served as the first capital of Canada.
Start off your visit on the 13th (Thu): explore the galleries of Martello Alley, explore the galleries of Fort Henry National Historic Site, get thoroughly spooked out with a ghost and vampire tour, then get a sense of history and politics at Kingston City Hall, and finally walk around Kingston Waterfront. Keep things going the next day: explore the world behind art at Agnes Etherington Art Centre, see the interesting displays at Canada's Penitentiary Museum, then contemplate the long history of Bellevue House National Historic Site, and finally look for all kinds of wild species at Lemoine Point Conservation Area.

To find other places to visit, more things to do, photos, and other tourist information, read Kingston trip itinerary planning app.

Traveling by flight from Toronto to Kingston takes 3 hours. Alternatively, you can take a bus; or drive. In October, daytime highs in Kingston are 17°C, while nighttime lows are 8°C. Wrap up your sightseeing on the 15th (Sat) early enough to drive to Ottawa.

Things to do in Kingston

Museums Historic Sites Parks
Highlights from your plan
Fort Henry National Historic Site ©
Fort Henry National Historic Site
Agnes Etherington Art Centre ©
Agnes Etherington Art Centre
Kingston Waterfront ©
Kingston Waterfront

3
nights
Ottawa, Canada

Ottawa ©
A major center of technology nicknamed "Silicon Valley North," Ottawa offers visitors a modern flavor with its range of trendy hotels, shops, and restaurants.
Ottawa is known for museums, nature, and fun & games. Your plan includes some of its best attractions: ponder the world of politics at Parliament Hill and Buildings, pause for some photo ops at Oscar Peterson Statue, learn more about the world around you at Canadian Museum of Nature, and see the interesting displays at National Gallery of Canada.

For reviews, ratings, where to stay, and tourist information, refer to the Ottawa vacation maker tool.

Getting from Kingston to Ottawa by car takes about 2.5 hours. Other options: take a train; or take a bus. In October, daytime highs in Ottawa are 16°C, while nighttime lows are 6°C. Finish your sightseeing early on the 18th (Tue) to allow enough time to take a train to Montreal.

Things to do in Ottawa

Museums Historic Sites Childrens Museums
Highlights from your plan
BATL - The Backyard Axe Throwing League ©
BATL - The Backyard Axe Throwing League
Parliament Hill and Buildings ©
Parliament Hill and Buildings
National Gallery of Canada ©
National Gallery of Canada

2
nights
Montreal, Canada

Montreal ©
Quebec's economic and cultural capital, Montreal serves as the province's major point of entry, known for its rich history and high standard of living.
On the 18th (Tue), make a trip to Notre-Dame Basilica, then admire the natural beauty at Montreal Botanical Garden, and then take in the spiritual surroundings of Saint Joseph's Oratory of Mount Royal. Get ready for a full day of sightseeing on the 19th (Wed): browse the fresh offerings at Jean-Talon Market, then learn more about the world around you at Biodome de Montreal, and then explore the world behind art at Musee des beaux-arts de Montreal.

To see where to stay, reviews, photos, and more tourist information, read Montreal trip planner.

Traveling by train from Ottawa to Montreal takes 2.5 hours. Alternatively, you can take a bus; or drive. Expect a daytime high around 17°C in October, and nighttime lows around 8°C. Wrap up your sightseeing by early afternoon on the 20th (Thu) to allow time for travel to Bennington.

Things to do in Montreal

Museums Parks Historic Sites
Highlights from your plan
Notre-Dame Basilica ©
Notre-Dame Basilica
Montreal Botanical Garden ©
Montreal Botanical Garden
Saint Joseph's Oratory of Mount Royal ©
Saint Joseph's Oratory of Mount Royal

3
nights
Bennington, United States

Bennington ©
Bennington is a town in Bennington County, Vermont, in the United States. Start off your visit on the 21st (Fri): get great views at Bennington Battle Monument, then admire the masterpieces at Williams College Museum of Art, then explore the world behind art at The Clark Art Institute, and finally admire the masterpieces at MASS MoCA. Get ready for a full day of sightseeing on the 22nd (Sat): admire the masterpieces at Bennington Museum, explore the different monuments and memorials at The Old First Church, then contemplate the long history of Hancock Shaker Village, and finally look for gifts at Bringing You Vermont.

To see traveler tips, maps, more things to do, and other tourist information, refer to the Bennington visit app.

Use the Route module to find suitable travel options from Montreal to Bennington. October in Bennington sees daily highs of 19°C and lows of 5°C at night. Cap off your sightseeing on the 23rd (Sun) early enough to go by car to Peru.

Things to do in Bennington

Museums Historic Sites Shopping

Side Trips

Williamstown, Hancock Shaker Village, MASS MoCA
Highlights from your plan
The Clark Art Institute ©
The Clark Art Institute
Bennington Battle Monument ©
Bennington Battle Monument
The Old First Church ©
The Old First Church

1
night
Peru, United States

Peru ©
Peru is a town in Bennington County, Vermont, United States. Start off your visit on the 23rd (Sun): stroll through Stratton Mountain Resort, stop by Vermont Country Store, then experience rural life at Taylor Farm, and finally take your sightseeing to a higher altitude at Bromley Mountain.

To find more things to do, where to stay, other places to visit, and more tourist information, read Peru trip website.

Getting from Bennington to Peru by car takes about an hour. October in Peru sees daily highs of 19°C and lows of 4°C at night. Finish your sightseeing early on the 24th (Mon) so you can travel to Arlington.

Things to do in Peru

Winter Sports Outdoors Parks

Side Trips

Stratton Mountain Resort, Taylor Farm, Vermont Country Store
Highlights from your plan
Bromley Mountain ©
Bromley Mountain
Vermont Country Store ©
Vermont Country Store
Taylor Farm ©
Taylor Farm

1
night
Arlington, United States

Arlington ©
Arlington is a town in Bennington County, Vermont, United States. Kick off your visit on the 24th (Mon): browse the exhibits of Hildene, The Lincoln Family Home, then stop by Northshire Bookstore, and then take in the dramatic scenery at Lye Brook Falls.

To find reviews, traveler tips, and other tourist information, read Arlington online itinerary planner.

Arlington is just a stone's throw from Peru. In October, daytime highs in Arlington are 19°C, while nighttime lows are 5°C. On the 25th (Tue), wrap the sightseeing up by early afternoon so you can travel to North Conway.

Things to do in Arlington

Parks Nature Historic Sites

Side Trip

Manchester
Highlights from your plan
Equinox Mountain ©
Equinox Mountain
Hildene, The Lincoln Family Home ©
Hildene, The Lincoln Family Home
Northshire Bookstore ©
Northshire Bookstore

4
nights
North Conway, United States

North Conway ©
North Conway combines colonial New England architecture with outlet shops selling goods from some of the world's most recognizable brands, all set amid the scenery of the White Mountains.
Take a break from North Conway with a short trip to Mount Washington Auto Road in Gorham, about 46 minutes away. There's lots more to do: admire all the interesting features of Kancamagus Highway, get some fabulous bargains at Settlers Green, take in the dramatic scenery at Diana's Baths, and take in the dramatic natural features at Cathedral Ledge.

To find where to stay, maps, ratings, and tourist information, read North Conway visit app.

Traveling by car from Arlington to North Conway takes 4 hours. In October, daytime highs in North Conway are 19°C, while nighttime lows are 8°C. Finish your sightseeing early on the 29th (Sat) to allow enough time to drive to Gilford.

Things to do in North Conway

Outdoors Parks Scenic Drive

Side Trip

Mount Washington Auto Road
Highlights from your plan
Kancamagus Highway ©
Kancamagus Highway
Mount Washington Auto Road ©
Mount Washington Auto Road
Diana's Baths ©
Diana's Baths

2
nights
Gilford, United States

Gilford ©
Gilford is a town in Belknap County, New Hampshire, United States. Lake Winnipesaukee has been added to your itinerary. Start off your visit on the 29th (Sat): look for all kinds of wild species at Squam Lakes Natural Science Center, then take your sightseeing to a higher altitude at West Rattlesnake Mountain, then stop by Beyond Obsession, and finally get great views at Abenaki Tower. Keep things going the next day: admire the striking features of Castle in the Clouds, then have some family-friendly fun at Funspot, and then get a new perspective on things with Boat Tours & Water Sports.

For other places to visit, photos, and tourist information, read our Gilford trip planner.

You can drive from North Conway to Gilford in 1.5 hours. In October in Gilford, expect temperatures between 18°C during the day and 6°C at night. On the 31st (Mon), wrap the sightseeing up by early afternoon so you can travel to Bar Harbor.

Things to do in Gilford

Parks Nature Wildlife

Side Trips

Moultonborough, Weirs Beach, Holderness, Lake Winnipesaukee, Hermit Woods Winery
Highlights from your plan
West Rattlesnake Mountain ©
West Rattlesnake Mountain
Castle in the Clouds ©
Castle in the Clouds
Squam Lakes Natural Science Center ©
Squam Lakes Natural Science Center

2
nights
Bar Harbor, United States

Bar Harbor ©
Bar Harbor is a town on Mount Desert Island in Hancock County, Maine, United States. Start off your visit on the 1st (Tue): hike along Ocean Path, take in the spiritual surroundings of St. Saviour's Church :, then contemplate the waterfront views at Frenchman Bay, and finally don't miss a visit to Land Bridge to Bar Island. On the 2nd (Wed), you'll have a packed day of sightseeing: paddle through the water with a kayaking and canoeing tour and then look for all kinds of wild species at Shore Path.

To find reviews, photos, traveler tips, and tourist information, read our Bar Harbor travel planner.

The Route module can help you plan travel from Gilford to Bar Harbor. In October in Bar Harbor, expect temperatures between 17°C during the day and 6°C at night. Cap off your sightseeing on the 2nd (Wed) early enough to go by car to Portsmouth.

Things to do in Bar Harbor

Parks Outdoors Adventure
Highlights from your plan
Shore Path ©
Shore Path
Frenchman Bay ©
Frenchman Bay
Kayaking & Canoeing

3
nights
Portsmouth, United States

Portsmouth ©
Portsmouth is a city in Rockingham County, New Hampshire, in the United States. Portsmouth is known for historic sites, parks, and museums. Your plan includes some of its best attractions: take an in-depth tour of Strawbery Banke Museum, see the interesting displays at USS Albacore Museum, make a splash at Water Country, and explore the galleries of John Paul Jones House.

To find more things to do, maps, where to stay, and more tourist information, read our Portsmouth trip itinerary builder site.

Traveling by car from Bar Harbor to Portsmouth takes 4.5 hours. Alternatively, you can do a combination of flight and bus; or do a combination of car, flight, and bus. In November, daytime highs in Portsmouth are 11°C, while nighttime lows are 0°C. Finish your sightseeing early on the 5th (Sat) so you can drive to Boston.

Things to do in Portsmouth

Parks Museums Historic Sites

Side Trips

Kittery Trading Post, Hampton Beach State Park
Highlights from your plan
Prescott Park ©
Prescott Park
Strawbery Banke Museum ©
Strawbery Banke Museum
Hampton Beach State Park ©
Hampton Beach State Park

3
nights
Boston, United States

Boston ©
Enjoy Boston some more: get to know the fascinating history of Freedom Trail, stroll around Rose Kennedy Greenway, admire the masterpieces at Museum of Fine Arts, and buy something for everyone on your list at Faneuil Hall Marketplace.

To see other places to visit, maps, ratings, and other tourist information, go to the Boston route planner.

Traveling by car from Portsmouth to Boston takes 1.5 hours. Alternatively, you can take a bus. Cap off your sightseeing on the 8th (Tue) early enough to travel to Chicago.

Things to do in Boston

Museums Parks Historic Sites
Highlights from your plan
Museum of Fine Arts ©
Museum of Fine Arts
Freedom Trail ©
Freedom Trail
Boston Public Garden ©
Boston Public Garden

3
nights
Chicago, United States

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Chicago is known for museums, parks, and nightlife. Your plan includes some of its best attractions: admire the masterpieces at The Art Institute of Chicago, engage your brain at Museum of Science and Industry, take a leisurely stroll along Navy Pier, and pause for some photo ops at Cloud Gate.

To find ratings, where to stay, reviews, and tourist information, read Chicago online travel route planner.

You can fly from Boston to Chicago in 4 hours. Other options are to do a combination of bus and flight; or drive. You'll gain 1 hour traveling from Boston to Chicago due to the time zone difference. In November, plan for daily highs up to 11°C, and evening lows to 1°C. Wrap up your sightseeing on the 11th (Fri) early enough to travel back home.

Things to do in Chicago

Museums Theme Parks Childrens Museums
Highlights from your plan
The Art Institute of Chicago ©
The Art Institute of Chicago
Millennium Park ©
Millennium Park
Skydeck Chicago - Willis Tower ©
Skydeck Chicago - Willis Tower

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