26 days in United States Itinerary

26 days in United States Itinerary

Created using Inspirock United States trip planner

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Route & dates

26 days in United States Itinerary

Start: Chicago
1
Chicago
— 1 night
Drive:  1​h 15​min
2
Beverly Shores
— 1 night
Drive:  15​min
3
Michigan City
— 1 night
Drive:  30​min
4
New Buffalo
— 2 nights
Drive:  2​h
5
Muskegon
— 2 nights
Drive:  30​min
6
Whitehall
— 1 night
Drive:  45​min
7
Pentwater
— 1 night
Drive:  30​min
8
Ludington
— 1 night
Drive:  45​min
9
Manistee
— 1 night
Drive:  1​h
10
Frankfort
— 4 nights
Drive:  1​h
11
Traverse City
— 2 nights
Drive:  1​h 15​min
12
Charlevoix
— 1 night
Drive:  30​min
13
Petoskey
— 1 night
Drive:  30​min
14
Harbor Springs
— 1 night
Drive:  1​h
15
Mackinaw City
— 1 night
ferry:  30​min
16
Mackinac Island
— 1 night
+2
Drive + Fly + Drive:  13​h 45​min
17
Manistique
— 2 nights
Drive:  6​h 15​min
End: Chicago

1
night
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Start off your visit on the 3rd (Tue): brush up on your military savvy at First Division Museum at Cantigny, then brush up on your military savvy at Cantigny Park, then take in the spiritual surroundings of Baha'i House of Worship, and finally take a stroll through Andersonville.

To see where to stay, more things to do, traveler tips, and other tourist information, use the Chicago driving holiday planning website .

Use the Route module to see travel options from your home to Chicago. In September, daytime highs in Chicago are 78°F, while nighttime lows are 61°F. On the 4th (Wed), wrap the sightseeing up by early afternoon so you can travel to Beverly Shores.

Things to do in Chicago

Museums Historic Sites Neighborhoods

Side Trips

Wheaton, Baha'i House of Worship
Highlights from your plan
Cantigny Park ©
Cantigny Park
Baha'i House of Worship ©
Baha'i House of Worship
First Division Museum at Cantigny ©
First Division Museum at Cantigny

1
night
Beverly Shores

Beverly Shores
Beverly Shores is a town in Pine Township, Porter County, Indiana, United States, about 36mi east of downtown Chicago. Kick off your visit on the 4th (Wed): enjoy the sand and surf at North Shore Beach.

For traveler tips, maps, more things to do, and other tourist information, refer to the Beverly Shores trip planner .

You can drive from Chicago to Beverly Shores in 1.5 hours. Traveling from Chicago in September, Beverly Shores is slightly colder at night with lows of 54°F. Finish your sightseeing early on the 5th (Thu) so you can travel to Michigan City.

Things to do in Beverly Shores

Beaches Parks Outdoors

1
night
Michigan City

Michigan City ©
Michigan City is a city in LaPorte County, Indiana, United States. On the 5th (Thu), get engrossed in the history at La Porte County Historical Society Museum, look for gifts at Stateline Blueberries, then tour the pleasant surroundings at Michigan City Beach, and finally take in the waterfront at Lighthouse & Pier.

To see other places to visit, where to stay, reviews, and tourist information, go to the Michigan City trip planning app .

Michigan City is just a stone's throw from Beverly Shores. In September, daily temperatures in Michigan City can reach 74°F, while at night they dip to 54°F. Wrap up your sightseeing on the 6th (Fri) to allow time to drive to New Buffalo.

Things to do in Michigan City

Beaches Parks Outdoors

Side Trip

La Porte County Historical Society Museum
Highlights from your plan
Stateline Blueberries ©
Stateline Blueberries

2
nights
New Buffalo

New Buffalo ©
New Buffalo is a city in Berrien County in the U.S. Kick off your visit on the 6th (Fri): take in the waterfront activity at Oselka Marina, then brush up on your knowledge of spirits at Journeyman Distillery, and then examine the collection at Hesston Steam Museum. Here are some ideas for day two: stroll around Galien River County Park, then do a tasting at St. Julian Winery-Union Pier, then do a tasting at Domaine Berrien Cellars, and finally admire the majestic nature at Grand Mere State Park.

To find photos, reviews, maps, and other tourist information, refer to the New Buffalo trip planning site .

New Buffalo is just a stone's throw from Michigan City. In September, daily temperatures in New Buffalo can reach 74°F, while at night they dip to 54°F. Finish up your sightseeing early on the 8th (Sun) so you can travel to Muskegon.

Things to do in New Buffalo

Parks Wineries Breweries & Distilleries

Side Trips

Hesston Steam Museum, Journeyman Distillery, Grand Mere State Park, Domaine Berrien Cellars, St. Julian Winery-Union Pier
Highlights from your plan
Galien River County Park ©
Galien River County Park
Grand Mere State Park ©
Grand Mere State Park
Domaine Berrien Cellars ©
Domaine Berrien Cellars

2
nights
Muskegon

Muskegon ©
Muskegon is a city in the U.S. Start off your visit on the 8th (Sun): steep yourself in history at USS LST 393, then explore the world behind art at Muskegon Museum of Art, and then explore the landscape on two wheels at Lakeshore Bike Trail. On your second day here, take an in-depth tour of Muskegon Heritage Museum, examine the collection at Lakeshore Museum Center, admire the natural beauty at The Monet Garden of Muskegon, examine the collection at Fire Barn Museum, then steep yourself in history at Hackley and Hume Historic Site, and finally look for gifts at The Cheese Lady.

Start your trip to Muskegon by creating a personalized itinerary on Inspirock.

Getting from New Buffalo to Muskegon by car takes about 2 hours. Due to the time zone difference, you'll lose 1 hour traveling from New Buffalo to Muskegon. In September in Muskegon, expect temperatures between 75°F during the day and 55°F at night. Finish your sightseeing early on the 10th (Tue) to allow enough time to drive to Whitehall.

Things to do in Muskegon

Museums Historic Sites Parks
Highlights from your plan
Muskegon Museum of Art ©
Muskegon Museum of Art
USS LST 393 ©
USS LST 393
Muskegon Heritage Museum ©
Muskegon Heritage Museum

1
night
Whitehall

Whitehall
Whitehall is a city in Muskegon County in the U.S. Kick off your visit on the 10th (Tue): kick back and relax at Meinert Park, do a tasting at Oceana Winery and Vineyard, then sample the tasty concoctions at Fetch Brewing Company, and finally examine the collection at Montague Museum.

For photos, reviews, maps, and more tourist information, read Whitehall trip planner .

Whitehall is just a stone's throw from Muskegon. September in Whitehall sees daily highs of 75°F and lows of 55°F at night. Finish your sightseeing early on the 11th (Wed) so you can drive to Pentwater.

Things to do in Whitehall

Beaches Parks Outdoors

Side Trips

Montague, Oceana Winery and Vineyard

1
night
Pentwater

Pentwater ©
Pentwater is a village in Oceana County in the U.S. Start off your visit on the 11th (Wed): explore the landscape on two wheels at William Field Memorial Hart-Montague Trail, do a tasting at The Fox Barn Winery, and then stroll around Silver Lake State Park Pedestrian Dune Access.

For other places to visit, reviews, traveler tips, and tourist information, read Pentwater trip website .

Drive from Whitehall to Pentwater in an hour. Expect a daytime high around 72°F in September, and nighttime lows around 52°F. Finish your sightseeing early on the 12th (Thu) to allow enough time to drive to Ludington.

Things to do in Pentwater

Parks Outdoors Beaches

Side Trips

Hart, The Fox Barn Winery
Highlights from your plan

1
night
Ludington

Ludington ©
Ludington is a city in the state of Michigan. On the 12th (Thu), identify plant and animal life at Nordhouse Dunes Wilderness, then have fun and explore at Port of Ludington Maritime Museum, and then play a few rounds at Hemlock Golf Club.

To find other places to visit, more things to do, traveler tips, and tourist information, read our Ludington trip itinerary planner .

Ludington is very close to Pentwater. Expect a daytime high around 72°F in September, and nighttime lows around 52°F. Finish your sightseeing early on the 13th (Fri) to allow enough time to drive to Manistee.

Things to do in Ludington

Outdoors Golf Wildlife
Highlights from your plan
Hemlock Golf Club ©
Hemlock Golf Club
Port of Ludington Maritime Museum ©
Port of Ludington Maritime Museum

1
night
Manistee

Manistee ©
Manistee is a city in the U.S. Start off your visit on the 13th (Fri): make a trip to Manistee North Pierhead Lighthouse, do a tasting at Douglas Valley Winery, then look for all kinds of wild species at Lake Bluff Bird Sanctuary, then steep yourself in history at S.S. City of Milwaukee/ USCGC Acacia, and finally stroll through Fifth Avenue Beach.

For more things to do, photos, other places to visit, and more tourist information, read our Manistee travel planning site .

Getting from Ludington to Manistee by car takes about an hour. In September, plan for daily highs up to 72°F, and evening lows to 51°F. Finish your sightseeing early on the 14th (Sat) to allow enough time to drive to Frankfort.

Things to do in Manistee

Parks Beaches Outdoors
Highlights from your plan
Lake Bluff Bird Sanctuary ©
Lake Bluff Bird Sanctuary
Fifth Avenue Beach ©
Fifth Avenue Beach
S.S. City of Milwaukee/ USCGC Acacia ©

4
nights
Frankfort

Frankfort ©
Frankfort is a city in Benzie County in the U.S. Visit Glen Haven Historical Village and Rogers Street Fishing Village for their historical value. Give yourself a bit of retail therapy at Ellie Harold Art Studio & Gallery and Crystal Lake Alpaca Farm and Boutique. Get out of town with these interesting Frankfort side-trips: South Manitou Island Lighthouse (in Glen Arbor) and Kewaunee (Parallel 44 Winery and Vineyard & Tug Ludington). And it doesn't end there: kick back and relax at Elberta Beach, get engrossed in the history at Benzie Area Historical Society & Museum, don't miss a visit to Elizabeth Lane Oliver Center for the Arts, and cast your line with a fishing tour.

To see ratings, reviews, more things to do, and tourist information, use the Frankfort sightseeing planner .

Drive from Manistee to Frankfort in an hour. In September, plan for daily highs up to 71°F, and evening lows to 53°F. Cap off your sightseeing on the 18th (Wed) early enough to go by car to Traverse City.

Things to do in Frankfort

Outdoors Parks Wildlife

Side Trips

Arcadia, Kewaunee, Elberta Beach, Rogers Street Fishing Village, South Manitou Island Lighthouse
Highlights from your plan
Rogers Street Fishing Village ©
Rogers Street Fishing Village
South Manitou Island Lighthouse ©
South Manitou Island Lighthouse
Benzie Area Historical Society & Museum ©

2
nights
Traverse City

Traverse City ©
Traverse City might be well known for its huge cherry industry, but its position along Grand Traverse Bay in Lake Michigan endows it with fine scenery and a wealth of outdoor attractions.
On the 18th (Wed), take in the exciting artwork at Michigan Artists Gallery, enjoy the sea views from Grand Traverse Lighthouse Museum, then learn about winemaking at Leelanau Wine Cellars, then do a tasting at Blustone Vineyards, and finally do a tasting at Mari Vineyards. On the 19th (Thu), you'll have a packed day of sightseeing: learn about winemaking at Left Foot Charley Winery, do a tasting at Rove Estate Tasting Room and Vineyard, learn about winemaking at Shady Lane Cellars, then learn about winemaking at 45 North Vineyard & Winery, and finally savor the flavors at Northern Latitudes Distillery.

For maps, traveler tips, ratings, and tourist information, read Traverse City trip site .

Getting from Frankfort to Traverse City by car takes about an hour. In September, daytime highs in Traverse City are 74°F, while nighttime lows are 54°F. Finish your sightseeing early on the 20th (Fri) so you can drive to Charlevoix.

Things to do in Traverse City

Wineries Museums Historic Sites

Side Trips

Lake Leelanau, Grand Traverse Lighthouse Museum, Shady Lane Cellars, Leelanau Wine Cellars
Highlights from your plan
Blustone Vineyards ©
Blustone Vineyards
Grand Traverse Lighthouse Museum ©
Grand Traverse Lighthouse Museum
45 North Vineyard & Winery ©
45 North Vineyard & Winery

1
night
Charlevoix

Charlevoix ©
Charlevoix is a city in the U.S. Start off your visit on the 20th (Fri): pick up some local products at John Cross Fisheries, then enjoy the sea views from Charlevoix South Pier Light Station, then look for all kinds of wild species at North Point Nature Preserve, and finally do a tasting at Royal Farms, Inc..

To find maps, where to stay, more things to do, and more tourist information, go to the Charlevoix trip itinerary planner.

You can drive from Traverse City to Charlevoix in 1.5 hours. Expect a daytime high around 70°F in September, and nighttime lows around 54°F. Cap off your sightseeing on the 21st (Sat) early enough to go by car to Petoskey.

Things to do in Charlevoix

Wildlife Parks Shopping

Side Trip

Royal Farms, Inc.
Highlights from your plan
North Point Nature Preserve ©
North Point Nature Preserve
John Cross Fisheries ©
John Cross Fisheries

1
night
Petoskey

Petoskey ©
Petoskey is a city and coastal resort community in the U.S. On the 21st (Sat), grab your bike and head to North Western State Trail, learn about winemaking at Walloon Lake Winery, do a tasting at Resort Pike Cidery and Winery, then learn about winemaking at Petoskey Farms Vineyard & Winery, then learn about winemaking at Maple Moon Sugarbush and Winery, and finally learn about winemaking at Crooked Vine Vineyard & Winery.

Plan a trip to Petoskey easily and quickly by telling Inspirock to suggest an itinerary.

Petoskey is just a short distance from Charlevoix. Expect a daytime high around 71°F in September, and nighttime lows around 52°F. Cap off your sightseeing on the 22nd (Sun) early enough to go by car to Harbor Springs.

Things to do in Petoskey

Wineries Parks Outdoors

Side Trip

Crooked Vine Vineyard & Winery
Highlights from your plan
Walloon Lake Winery ©
Walloon Lake Winery
Maple Moon Sugarbush and Winery ©
Maple Moon Sugarbush and Winery

1
night
Harbor Springs

Harbor Springs ©
Harbor Springs is a city and resort community in Emmet County in the U.S. Kick off your visit on the 22nd (Sun): identify plant and animal life at Thorne Swift Nature Preserve, learn about winemaking at Pond Hill Farm Winery, then learn about winemaking at Pleasantview Vineyards & Winery, and finally identify plant and animal life at The Oden State Fish Hatchery.

To see ratings, reviews, and tourist information, read Harbor Springs trip app .

Harbor Springs is very close to Petoskey. Expect a daytime high around 71°F in September, and nighttime lows around 52°F. Finish your sightseeing early on the 23rd (Mon) to allow enough time to drive to Mackinaw City.

Things to do in Harbor Springs

Wildlife Wineries Parks

Side Trip

The Oden State Fish Hatchery
Highlights from your plan
Thorne Swift Nature Preserve ©
Thorne Swift Nature Preserve

1
night
Mackinaw City

Mackinaw City ©
Mackinaw City is a village in Emmet and Cheboygan counties in the U.S. Kick off your visit on the 23rd (Mon): take a tour of Shepler's Lighthouse Cruises, then see the interesting displays at Great Lake Light House Keepers, and then explore the wealth of natural beauty at Headlands International Dark Sky Park. On your second day here, look for gifts at Marshall's Fudge and Candy Company, stroll around Gary R Williams Memorial Park, enjoy the sand and surf at Nancy Dagwell Campbell Park, then stroll around Maritime Park, then get engrossed in the history at Heritage Village at Mackinaw, and finally shop like a local with Three Pines Studio.

To find more things to do, ratings, other places to visit, and more tourist information, you can read our Mackinaw City trip site .

You can drive from Harbor Springs to Mackinaw City in an hour. In September in Mackinaw City, expect temperatures between 67°F during the day and 54°F at night. Finish your sightseeing early on the 24th (Tue) to allow enough time to ride a ferry to Mackinac Island.

Things to do in Mackinaw City

Parks Nature Museums

Side Trip

Three Pines Studio
Highlights from your plan
Headlands International Dark Sky Park ©
Three Pines Studio ©
Three Pines Studio
Heritage Village at Mackinaw ©
Heritage Village at Mackinaw

1
night
Mackinac Island

Mackinac Island
Mackinac Island is a city in Mackinac County in the U.S. On the 25th (Wed), enjoy the sea views from Round Island Lighthouse, look for gifts at Island House Bike Shop, then contemplate the long history of Fort Holmes, then pause for some serene contemplation at St Anne's Catholic Church, and finally identify plant and animal life at Wings of Mackinac Butterfly Conservatory.

To find out how to plan a trip to Mackinac Island, use our trip itinerary maker.

Mackinac Island is just a stone's throw from Mackinaw City. Expect a daytime high around 67°F in September, and nighttime lows around 54°F. Finish up your sightseeing early on the 25th (Wed) so you can travel to Manistique.

Things to do in Mackinac Island

Historic Sites Wildlife Parks
Highlights from your plan
Fort Holmes
Fort Holmes
St Anne's Catholic Church ©
St Anne's Catholic Church

2
nights
Manistique

Manistique ©
Manistique, formerly Monistique, is the only incorporated city in and the county seat of Schoolcraft County of the U.S. Do some cultural sightseeing at Peninsula Point Lighthouse and Mackinaw Trail Winery. Give yourself a bit of retail therapy at Lake Effect Art Gallery and The Mustard Seed. Change things up with these side-trips from Manistique: Munising (Chapel Falls, Tannery Falls, & more), Sand Point Lighthouse (in Escanaba) and Chapel Falls (in Grand Marais). Next up on the itinerary: contemplate the waterfront views at Indian Lake, learn about winemaking at Garden Bay Winery, and experience rural life at Thompson State Fish Hatchery.

For ratings, photos, more things to do, and other tourist information, you can read our Manistique holiday builder website .

Explore your travel options from Mackinac Island to Manistique with the Route module. Traveling from Mackinac Island in September, expect slightly colder with lows of 49°F in Manistique. Wrap up your sightseeing on the 28th (Sat) early enough to travel back home.

Things to do in Manistique

Nature Parks Historic Sites

Side Trips

Munising, Chapel Falls, Garden Bay Winery, Sand Point Lighthouse, Peninsula Point Lighthouse
Highlights from your plan
Chapel Falls ©
Chapel Falls
Peninsula Point Lighthouse ©
Peninsula Point Lighthouse
Tannery Falls ©
Tannery Falls

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