“The Most Perfect Road Trip” In Detail, From Chicago (part one)

This page is being shared on social media like crazy promising a road trip across the 48 contiguous United States.  I’m setting fourth to create a more detailed plan starting and ending from Chicago.

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Day One

If you’re in the Chicago area, start by taking I-55 south to Springfield.  This is actually a pleasant drive and takes you through quite a few Route 66 towns.  Although these aren’t on this ‘perfect road trip’ map, feel free to comment me and I’ll provide you with details on the Chicago-Springfield Route 66 leg.

The Most Perfect Road Trip from Chicago, Chicago to Springfield

In Springfield, you’ll want to check out:

Abraham Lincoln’s Presidential Library and Presidential Museum

Cozy Dog Drive In

Lincoln Home National Historic Site

Lincoln Tomb

Lincoln’s New Salem (yes please!)

Route 66 Twin Drive In

The Most Perfect Road Trip, Springfield

From Springfield, you’ll head toward Effingham en route to French Lick.

Most Perfect Road Trip, Springfield to French Lick

In Effingham, Firefly Grill is worth the stop;  as is the Cross at the Crossroads.  Keep pushing through and strive to arrive at West Braden Springs Hotel.  If you arrive here late on day one, I’d plan on staying here for the night.  French Lick Springs Hotel is adjacent and either one is a great stop.

Most Perfect Road Trip, West Baden Springs

Day 2

You’ll spend the first part of the day here at West Baden Springs and French Lick.  Things to do include:

Exploring both West Baden Springs Resort and French Lick Resort

Downtown French Lick

French Lick Scenic Railway

Grab lunch at Mikki’s Deli and Sweet and get ready to hit the road.  The goal is to arrive at Monmouth Cave by evening.

Most Perfect Road Trip, French Lick West Baden

Santa Claus, Indiana might be worth stopping at since there’s really no rush to Monmouth Cave.  Things to check out here include:

Holiday World

Santa Claus Christmas Store

Santa Claus Post Office

Most Perfect Road Trip, French Lick to Monmouth Cave

Onward, continue south to the Monmouth Cave Hotel.  Like the French Lick Hotel, I have personally stayed here.  It’s not grand like the national park lodges of the west, but there is something special about this place.  They do serve dinner onsite until 8pm.  Relax and enjoy the hotel.


Day 3

Begin your day with some breakfast at either the hotel or at a local restaurant.  After that, check out one of the tours at Monmouth Cave National Park.  I’ve done the basic tour and another more extensive tour.  I’m the type that gets nervous with new situations and I managed the lengthy tour just fine.  This might be a once in a lifetime experience, so I’d strongly think about doing a longer tour.

Ultimate Road Trip- Monmouth Cave

Hop in the car and head toward Louisville.  Check out the official Louisville Visitor Center site for some ideas.  The Louisville Belle is my favorite!

Most Perfect Road Trip, Monmouth Cave to Spring Grove Cemetery

Next up is Spring Grove Cemetery in Cincinnati, Ohio!  I’m not a fan of cemeteries, but this was on the original road trip map I decided to include it.  Spring Grove Cemetery is the second largest cemetery in the United States and embodies a garden/arboretum feel.  Bypass the rest of Cincinnati and continue toward Detroit.  Honestly, you might not make it all the way to Detroit.  Don’t push it too much.  Aim for as close to Detroit as you can.

Most Perfect Road Trip, Spring Grove Cemetery

Most Perfect Road Trip, Spring Grove Cemetery to Detroit

End your day in a hotel as close to Detroit as possible.  Options might include:

Residence Inn Livonia

Fairfield Inn Toledo North

Courtyard Dearborn


Day 4

Good morning Detroit!  The highlight here from the original article is the Fox Theater which is the largest surviving theater from the 1920s.  That being said, it’s probably best to see a show here (if possible) so I’m going to make Detroit a two night stop over.  Here are some ways to spend the day in Detroit.

Anna Scripps Whitcomb Conservatory

Detroit Princess Riverboat

Detroit PeopleMover

Kids Rock Music Lab

Henry Ford Museum

Legoland Discovery Center

Most Perfect Road Trip: Detroit



Green Lantern Pizzeria


Eos Cafe and Coffee House


Wrap up your day at the Fox Theater.


Day 5

Wake up, grab something quick to eat, and hit the road!  Today, you’ll be making a stop in Cleveland en route to Niagara Falls.

Most Perfect Road Trip, Detroit to Cleveland

Activities in Cleveland include:

Rock and Roll Hall of Fame

Cedar Point Amusement Park

Cleveland Botanical Garden

Cuyahoga National Park

Pro Football Hall of Fame


Mabel’s BBQ

Melt Bar and Grill

Most Perfect Road Trip, Cleveland

Most Perfect Road Trip, Cleveland to Niagara Falls

Niagara Falls:

Maid of the Mist

Niagara Falls State Park

Most Perfect Road Trip, Niagara Falls


The Giacomo

Niagara Falls Marriott Fallsview



Blueline Diner


Day 6

Today is going to be jam packed!  You’ll stop in Syracuse on your way to Shelburne Farm, Vermont, and end (probably very late) at the Mount Washington Resort in New Hampshire.  Leave Niagara Falls by 9am and you’ll be in Syracuse by noon.  Spend an hour in Syracuse and then get back on the road.  You should get to Shelburne around 5:30pm.  Check out the farm and grab dinner in their seasonal restaurant.  Push through and you’ll arrive at Mount Washington Resort in New Hampshire.

Most Perfect Road Trip, Niagara Falls to Syracuse

Activities in Syracuse:

Armory Square

Destiny USA


Funk n Waffles

Kitty Hoynes

Most Perfect Road Trip, Syracuse


Most Perfect Road Trip, Syracuse to Shellburne Farms

Shelburne Farms, Vermont is a massive property located on the shores of Lake Champlain and focuses on sustainable agriculture and sustainable forestry.  This is a destination in itself with its seasonal inn and restaurant, walking trails, tours, and farmyard.  Arrive in time for dinner.

Shelburne Inn

Most Perfect Road Trip, Shelburne Farms

After soaking in all that Shelburne Farms has to offer, finish your day by arrive at Mount Washington Resort in New Hampshire.

Most Perfect Road Trip, Shellburne Farms to Mount Washington Resort


Day 7

Wake up and spend the first part of the day exploring Mount Washington Resort.  This resort has been a favorite of presidents for decades and is yours to explore this morning.  Depending on the season you visit, there are MANY activities to indulge in including the spa, zip lining, river tubing, and scenic lift rides.

Most Perfect Road Trip, Mount Washington Resort

Next, you’ll head into Maine towards Acadia National Park where you’ll spend two nights. Acadia National Park is where the mountains meet the sea and it is absolutely STUNNING!  Depending on how much time you spend at the Mount Washington Resort, you might get to Acadia pretty late.  There are a handful of quintessential seaside towns to stay in, and I recommend Bar Harbor.  Let’s talk accommodations!  So there are some pretty cute B&Bs, but I’m not personally recommending any because I’m just not of fan of that type of accommodation.  The hotel I recommend is the Bluenose.  The Bar Harbor Inn is also an excellent choice.  Cottages are another option, but it might be difficult to find one that rents by the night.

Most Perfect Road Trip, Mount Washington Resort to Bar Harbor (Acadia National Park)

If you arrive in Bar Harbor early enough, definitely check out the town.  There are lots of restaurants and bars.


Day 8

Acadia National Park is yours for the entire day!  There are lots of options here so it’s probably best to check out this website.  Definitely check out one of the visitor centers before you venture out anywhere.  If you don’t like the idea of tackling a national park on your own, you might want to consider a guided tour.  Acadia National Park offers pretty much any type of tour you want including TROLLEY, boat, kayak, bike, and air tours.  If you’re more the independent type, there are 125 miles of hiking trails.  Several opportunities for whale watching are available.  There are other types of activities as well.  After a long day in the national park, consider visiting the spa at either Bluenose  or Bar Harbor Inn.  End your day either in Bar Harbor or in a neighboring town.


Most Perfect Road Trip, Acadia National Park and Bar Harbor


Day 9

Today is fun filled!  Hit the road as early as possible toward Boston.  First, you’ll visit the USS Constitution.  Also known as “Old Ironsides” this boat was best known for it’s role in the War of 1812.  If you’re wanting to spend a decent amount of time in Boston, consider getting the city pass.

Boston Attractions:

Freedom Trail

Boston Tea Party Ships and Museum 

Fenway Park

Newberry Street

Most Perfect Road Trip, Boston

Boston Restaurants:

Sam LaGrassa’s

Italian Express Pizzeria

Most Perfect Road Trip, Bar Harbor to Boston

Most Perfect Road Trip, Boston to Newport

After exploring Boston, you’ll head toward Newport, Rhode Island.  You’ll arrive in time to check in to your hotel and enjoy some local fare for dinner.

Newport Hotels:

Newport Marriott

Hotel Viking

Newport Residence Inn

Most Perfect Road Trip, Newport


Newport Restaurants:

Rosemary and Thyme Cafe

The Corner Cafe

Midtown Oyster Bar



Stay tuned for part 2 where we start at the Breakers in Newport!


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