Illinois is where the Mother Road begins! Connecting Chicago to St. Louis, 301 miles of Route 66 stretch between these two cities. You'll encounter charming towns filled with vintage diners and many beautifully restored filling stations. It's a state of giants, unusual roadside photo-ops, and museums that bring the past to life. In Illinois, you'll experience a nostalgic yesteryear with classic Midwest Americana as you drive past expansive prairies and iconic neon. There's a wealth of history and much to explore here as you set out for adventure on your All-American road trip down the Mother Road.
Illinois Route 66 has been awarded an All-American Road designation, the highest National Scenic Byway designation. This article will guide you through the BEST gems of Illinois Route 66, so you'll be prepared for an unforgettable, fun-filled journey of historical treasures and memories.
Route 66 played a pivotal role in our nation's development, weaving its path through eight states: Illinois, Missouri, Kansas, Oklahoma, Texas, New Mexico, Arizona, and California. It left an unforgettable imprint on America's physical, historical, and cultural fabric. No other highway embodied the spirit of hope, freedom, and the American Dream like Route 66.
It all started with Cyrus Avery, a visionary businessman from Oklahoma who dreamed of a road cutting diagonally across the country from Lake Michigan to the Pacific Ocean. This route connected numerous rural towns, granting small communities access to a national highway network. Officially designated as Route 66 in 1926, Avery dubbed it the Main Street of America.
Post-World War II aspirations for faster, safer roads led authorities to construct four-lane alignments bypassing small towns accustomed by then to heavy traffic-driven commerce activities around them. By 1977, Interstate 55 had entirely replaced Route 66 through Illinois, and in 1985, the federal government decommissioned it.
Yet, the legacy lives on today, offering intrepid visitors more than 300 miles worth exploring in Illinois, including original segments laid back in 1926. Preserved historically significant structures help bring alive experiences reminiscent of those early days while authentic businesses relish opportunities to serve modern-day adventurers traversing this historic highway. Tales abound about legendary figures inhabiting classic locations dotting this storied landscape where swapping stories becomes the norm among seasoned roadies and first-time explorers alike. The History of Illinois Route 66![]()
One of the Illinois Legends, this recreated neon sign can be seen at the Route 66 Experience in Springfield.
In 1953, the Bel-Air Drive-In was established by Komm Theaters in Mitchell, featuring a single screen along the famed Route 66. A second screen was added in 1979, allowing the drive-in to host around 700 cars at its peak. However, the drive-in ceased operations in 1987 and was torn down in the mid-1990s. The vibrant neon marquee remained at the entrance for over three decades after its closure. In 2018, it was removed and sold to sign collectors, who eventually dismantled it and distributed its parts among various collectors.
Illinois already had the Pontiac Trail, which linked many of the "main streets" between Chicago and St. Louis. Funded by State Bond Issue 4 in 1920, constructing this road between the two cities was the first step toward more efficient highway travel in the state.
From Chicago's Palmer House Hilton to Granite City's Apple Valley Motel; from Louis Mitchell’s Restaurant in Chicago to Litchfield’s Ariston Café; from Odell’s Standard Oil Station to Mt. Olive's Soulsby Station—businesses lined up along Route 66 eager to serve its travelers with warmth alongside their goods or services. Illinois is doing something that no other Route 66 state has done by attempting to preserve three active alignments of the Mother Road.
with horses, horse-drawn vehicles, and tractors; the average speed limit was 25 mph. This alignment passes through many small towns since mechanical problems were frequent for the new-fangled automobile.
The era of prohibition, from 1920 to 1933, had a significant impact on Route 66. The all-weather road created in 1924 made transportation of illegal alcohol possible year-round. Production stills in central and southern Illinois used Route 66 to ship alcohol to Chicago and St. Louis speakeasies, adding a layer of intrigue to the road's history.
The 1940-1977 Alignment
With WWII raging in Europe, President Roosevelt studied how well the US highways met our defense needs. The results from that study played a significant role in the 1951 alignment of Route 66, its most extensive redesign yet. The 1956 Highway Act marked a significant turning point in Route 66's history. Construction on the Interstate Highway System began, and by the end of 1956, sections of Route 66 were replaced by Interstate 55 as the main transportation route to the West. This marked the beginning of the end for the Illinois Mother Road, and all Route 66 signage was gone by January 1977. The entire road was decommissioned in 1985, a momentous event in the history of American road culture.
Here's a travel tip: While traveling through Illinois, you might encounter intersections where the three alignments split off in different directions. When in doubt, I generally opt for the oldest alignment since that alignment will take you through the town, as Route 66 was initially designed to do.
Because of the three alignments, writing this article has been challenging. I can't help but chuckle when people mention they drove Route 66 through Illinois and didn't think there was much to see. It usually turns out they mostly stayed on I-55, which is very disappointing.
Trust me, that's not the case at all. In 2022, it took me over six months of weekends to thoroughly explore all three alignments and truly see it all. Despite this, I've missed numerous museums and restaurants because of seasonal closures.
ChicagoWhere It All Begins - Grant Park
Many people mistakenly believe Grant Park marks the eastern end of historic Route 66. Because of this, Buckingham Fountain, one of the park's most iconic landmarks, is often thought to symbolize the beginning of the Mother Road. But Buckingham Fountain was actually built a year after the highway opened. While it is close, historically, the starting point was at the junction of Jackson Boulevard and Michigan Avenue.
Even so, since they are only 0.4 miles apart, it's worth stopping.
Buckingham Fountain is one of the largest fountains in the world. Designed in a Rococo wedding cake style, it is inspired by the Latona Fountain at Versailles, yet it is double the size of its muse. It boasts four groups of Art Deco seahorses that symbolize the four states surrounding Lake Michigan—Illinois, Wisconsin, Michigan, and Indiana. The pool itself represents Lake Michigan. Officially named the Clarence Buckingham Memorial Fountain, Kate Sturges Buckingham commissioned this fountain to memorialize her brother Clarence.
From mid-April to mid-October, the fountain operates from 8 a.m. to 11 p.m. During the day, there is a water jet performance, and at night, there is a vibrant evening light display. The 20-minute fountain shows are every hour on the hour, with the last show being at 10pm.
The Three Begin Signs
Start at the intersection of East Adams Street and Michigan Avenue.
East Jackson Boulevard at Michigan Avenue Down Jackson, a short distance beyond the CVS Pharmacy.
Parking in Chicago
If you get a very early start on the weekend, it should be easy enough to pull over and snap a few quick shots at one of the Route 66 Begin signs, but during the week, the traffic may make that difficult. If you wish to explore the area, you must use a parking garage and walk. I recommend the Grant Park South Parking Garage. It is the closest parking garage to Michigan Avenue's Route 66 Begin and End signs. It is only 300 feet from this garage to the Art Institute and 4/10 of a mile to Buckingham Fountain. Be aware that parking in the Chicago Loop is expensive without advanced planning, but if you use SpotHero or Millennium Garages to reserve parking, they can save you 50% or more. For example, the day I visited, I used SpotHero and paid $15 for 12 hours. The rate chart inside the garage for 12 hours of parking was $40. Lou Mitchell's Restaurant - 565 West Jackson Blvd
Lou Mitchell’s Restaurant is a historic Route 66 institution. Strategically located just a few blocks from the eastern terminus of the Mother Road, Jackson Boulevard was the starting point until 1955, when it was made a one-way street in the opposite direction.
The diner first opened in 1923 across the street from its current location. William Mitchell named his new restaurant after his son, Lou, who eventually took over the family business running it until he was well into his 70s. In 1992, Lou sold the restaurant to his niece. On the exterior, the intense presentation of neon, shining glass, and sleek aluminum places this historic eatery in the Golden Age of Route 66. The restaurant has two signs originating from the 1949 relocation: a neon sign proclaiming “Lou Mitchell’s Serving the World’s Best Coffee” stretches across the entire building length, and one advertising the restaurant’s handmade bakery goods hangs off to the side. On the inside, not much has changed since the restaurant opened. The dining room still has the original tables, coat racks, and seating, and the floor retains its original black and white terrazzo flooring, immediately transporting you back to the heydays of Route 66. Known for its excellent breakfast and lunch fare, Lou’s was already feeding the hungry when Jackson Boulevard was designated Route 66 in 1926. While it was already popular with the locals, it became known as the first stop to eat before heading across the country on the Mother Road. As a result, Lou Mitchell’s was often crowded with long lines of people stretching out the front door. Keeping with the tradition, the staff still passes out freshly baked donut holes and Milk Duds to all female guests and children to ease the wait. The Berghoff Restaurant - 17 West Adams
German immigrant Herman Joseph Berghoff opened the Berghoff Restaurant in the center of the Chicago Loop in 1898. Initially a saloon, he established the business to popularize family-owned Berghoff Beer.
It placed the restaurant very near the Mother Road's starting point. As a result, Berghoff's became one of the popular starting points for many Route 66 travelers.
While in Chicago, here are a few other places and activities you might be interested in...
Millennium Park - home of the Cloud Gate AKA The Bean Willis Tower - 233 S Wacker Dr Art Institute of Chicago - 111 S Michigan Ave Museum of Science & Industry - 5700 S DuSable, Lake Shore Dr The Magnificent Mile - Michigan Avenue Lincoln Park Zoo - Parking lot entrance - 2400 N. Cannon Drive Navy Pier - 600 E Grand Ave Take a River Cruise Cicero
Henry's Drive-In - 6031 Ogden Ave
In its early days, a visionary entrepreneur, Bill Henry sold kosher hot dogs part-time from a mobile stand near Ogden Avenue and Austin Boulevard. By 1950, his passion and dedication led to establishing a small diner with six stools and walk-up windows, which he soon turned into his full-time business. Henry's Drive-In expanded as the landscape of fast food changed with the arrival of a new McDonald's nearby.
The drive-in offers classic Chicago-area hot dog stand fare: Italian beef sandwiches, Italian sausage sandwiches, combo Italian beef and sausage sandwiches, and Tom-Tom tamales on buns topped with chili. However, their standout offering is the Chicago-style hot dog topped with fries—a dish celebrated by the fiberglass display on their iconic sign. The typical Chicago-style hot dog features a Vienna Beef frank nestled in a poppy seed bun adorned with yellow mustard, chopped onions, relish, dill pickle spears, tomatoes, pickled peppers, and celery salt—it's often described as being topped with a salad. The large hot dog sign outside resembles what some call an original Chicago Hot Dog or a Depression Dog. This term refers to the Great Depression when hot dogs were a popular and affordable meal. The Depression Dog is topped with onion, relish, mustard, peppers, and fries wrapped in wax paper. Inside the diner are many nods to its Route 66 history, including signs, old pictures, and plenty of interesting memorabilia. Willowbrook
Dell Rhea Chicken Basket - 645 Joliet Road
The Chicken Basket's origins date back to the 1930s, when it functioned as a lunch counter attached to a gas station in rural Hinsdale. This blend of services was typical along Route 66, where businesses often operated with slim profit margins and had to innovate to attract patrons.
According to legend, two local farm women approached Irv Kolarik with an enticing proposition. If he agreed to buy chickens from them, they would share their exceptional fried chicken recipe and teach him to fry it. Eventually, the gas station faded into history as the Chicken Basket took center stage. In 1946, Kolarik built the restaurant in its current location next door to the original lunch counter. The restaurant still looks much the same inside and out, with its original neon sign. Facing challenges brought forth when the Interstate cut through Hinsdale in 1962, traffic dwindled rapidly, causing the demise of many businesses. At one point, the Chicken Basket faced foreclosure. Still, it narrowly escaped thanks to its new owner, Delbert (Dell) Rhea, who had a new marketing strategy targeting the suburbs and travelers alike to save the business. Romeoville
White Fence Farm - 1376 Joliet Road
While there are several White Fence Farm locations, the original is on Route 66 in Romeoville, and the menu has remained unchanged since the 1950s.
Bob Hasert, Sr. and his wife, Doris, were already serving fried chicken at their Harmony House restaurant in Aurora, Illinois, when they discovered the 450-acre White Fence Farm on a drive down Route 66. Back then, the place was mostly known for the classic cars parked out front. Billionaire Sylvester Peabody of Peabody Coal owned it then and used it to house coal miners. The property included a restaurant with a shuffleboard court, which Bob thought was a perfect way to pass the time while waiting for a table. The Hasterts bought the property and introduced their fried chicken recipe from their other restaurant. Before long, White Fence Farm gained fame for its crispy fried chicken dinners, which are served family-style. The farm's name and the Hastert family's recipe have remained unchanged. Fresh whole chickens still arrive daily from the farm, where employees hand-cut them. They claim the secret to their unique taste lies in their cooking method. After the chicken is coated with flour milled exclusively for them, it’s cooked in a pressure cooker. Then, upon order, it’s flash-fried for 2 to 3 minutes to achieve a crispy golden-brown skin. Served family style, a meal consists of four pieces of chicken per person. It is accompanied by old-fashioned favorites like pickled beet relish, kidney bean salad, coleslaw, and homemade corn fritters dusted with powdered sugar. Not feeling like chicken, other options on the menu include broiled Icelandic fish, fried shrimp, or T-bone steaks. White Fence Farm is not just a restaurant. It's an experience. With several dining rooms and the ability to seat over one thousand guests at a time, it's a place where memories are made. The farm also boasts several nostalgic exhibits, including an antique car collection. Outside, the farm comes to life with friendly farm animals, such as alpacas, miniature goats, and pet chickens, just waiting to be fed or petted through the fence. It's a place where the past meets the present and where every visit is a unique adventure. Joliet
Joliet was integral to the original Route 66 path. This section of Route 66 primarily follows today's IL 53, but the highway was rerouted through Plainfield in 1940. Segments of Route 66 through Joliet run alongside the I&M Canal (Illinois & Michigan Canal State Trail) and the Lincoln Highway.
Rich & Creamy - 920 North Broadway St
Part of the Joliet Kicks on 66 Park, the Rich & Creamy, is typical of the ice cream stands that dotted the Mother Road back in the day. This building has been around since 1965 but didn't become an ice cream stand until 1977. The city purchased the building as part of the Broadway Greenway project in the early 2000s.
Just across the street from the Route 66 Park is Dick's Towing.
Dick's on 66 - 911 North Broadway Street
This place is cute and worth a quick stop to look around!
Dick’s on 66 has been the home of Dick’s Towing Service since 1976. The building, an artistic reimagining of an old autobody shop, features cars on the roof and a 1950s-era police car out front. They even have a section of the original road brick framed off for you to stand on. Joliet Historical Museum & Route 66 Welcome Center - 204 North Ottawa Street
The Joliet Historical Museum and Route 66 Welcome Center is a great stop, especially if you decide to skip Chicago, which I know many Route 66 travelers do. You can pick up all the Illinois Route 66 travel brochures here, and they have a great gift shop. I was impressed with their museum, too.
Be sure to pick up a Route 66 Soda in the gift shop. If you're like me, you'll have to try them all before you make it to the end of the Mother Road. I think Cream and Black Cherry are my faves! Rialto Square Theatre - 102 N Chicago Street
during the most prolific period of their career to design the theatre. With seating for 2000, it was the largest and most elegant vaudeville theatre ever built in Illinois outside Chicago. The décor is luxurious, with a rotunda modeled after Rome's Pantheon and an inner lobby based on Versailles' Hall of Mirrors. It became the centerpiece of Joliet's downtown and is considered one of the most beautiful theatres in the nation. It is on the American Institute of Architects' list of "150 Great Places in Illinois."
It was one of Al Capone's favorite hangouts. Over the years, it has hosted performances by Andy Williams, Mitzi Gaynor, Red Skelton, Victor Borges, Liberace, and hundreds of other famous names. Today, musicals, plays, concerts, and standup comedy can be seen at the theatre. The Rialto was closed in the mid-1970s and saved from demolition. It was placed on the National Register of Historic Places in 1978 and restored to its original grandeur in the 1980s. Wilmington
Gemini Giant - 201 Bridge Street
In 1960, John and Bernice Korlic purchased an already-established hotdog and ice cream shop on Route 66 in Wilmington. They renamed it the Launching Pad Drive-In since it was the Atomic Age, and everyone was crazy about everything related to space and space exploration.
Giant through a local naming contest in honor of the Gemini space missions. The Korlic family ran the restaurant for 47 years, finally selling it in 2007.
The Gemini Giant was recently restored and moved to its new location. In 2000, it was inducted into the Illinois Route 66 Hall of Fame. Braidwood
Polk-A-Dot Drive-In - 222 N Front Street
The Polk-A-Dot Drive-In is a family-owned 1950s diner. When it opened in 1956, it operated out of a white polka dot spotted bus. As money and time allowed, the owner built a small building with walk-up windows and later added the dining room for eat-in. Although they are now inside the building, those original walk-up windows are still where you order your food today.
The diner's interior has been extensively remodeled with neon and 50s décor collected from other local businesses, and the walls are covered in photos of 50s icons. This place is cute as a button, and it will make you feel like you forgot to put on your bobby-socks and poodle skirt that morning!
When you visit, be sure to order a hamburger and Green River float. Allow a little time to take it all in and drop a quarter in the tabletop jukebox.
Be sure to make a trip to the bathroom while you are there; I'll leave that as a surprise!
A well-known Route 66 gem, the Polk-A-Dot Drive-In, was inducted into the Route 66 of Illinois Association's Hall of Fame in 2002. Dwight
The village of Dwight has a fascinating history; it's worth taking the time to walk the downtown and explore it.
Ambler-Becker Texaco - 417 W Waupansie
The gas station built in 1933 by Jack Schore was a cottage-style station with wood clapboard siding and an arched roof. Residential windows with shutters and flower boxes underneath gave it a homey appearance, and a canopy extending out from the office sheltered the three Texaco gas pumps. Mr. Schore also had an ice house on the property.
In 1936, Vernon Von Qualen leased the station, changing the name to Vernon’s Texaco Station. Over the next two years, Qualen purchased the station from Schore before selling it to Basil “Tubby” Ambler in 1938. Tubby Ambler owned the station from 1938 to 1966, changing the name to Ambler Texaco. He added the concrete block service bays to the north side of the building in the early 1940s, following the national trend to provide a full-service garage. Phil Becker, the last gas station owner, lived six houses down and started working for Tubby Ambler as a young child running errands. By the time he was 14 or 15 years old, Tubby had hired him to watch the station on Sundays so Tubby could go to gun shows. Becker continued to work at the gas station through its subsequent owners, Earl Koehler, and Royce McBeath, before purchasing the station from McBeath in 1970, just a month after getting married. Phil Becker operated the station for over 26 years, first as a Texaco and later as a Marathon Gas Station, finally closing it in 1999. He continued as an auto repair shop until 2002, when he gave the station to the village of Dwight. When the station closed, it was the longest continuously operated gas station along the Mother Road. The gas station and office have been restored to their 1930s appearance, and the service bays were restored to the 1940s. In 2007, the station reopened as a Route 66 Visitors Center. Odell
Subway Tunnel - 313 West Hamilton
Across the street from St. Paul’s Catholic Church in Odell is what remains of a pedestrian tunnel that once ran under the road on Route 66's 1926 - 1946 alignment.
Standing on the corner in this quiet little village, it is hard to imagine that traffic was once so congested that parishioners and schoolchildren needed a Subway, as it was called by the locals, to cross the street safely on their way to school or church. After 1947, Route 66 became a four-lane highway, bypassing the town two blocks to the west. As a result, the Subway was no longer needed, and its entrance was sealed off in the 1950s. In 2006, the Route 66 Association of Illinois restored the railing and first three steps of the tunnel because of its importance to Route 66's history. Standard Oil Gas Station - 400 S West Street
Constructed in 1932 by contractor Patrick O'Donnell, this Standard Oil station's design is based on the 1916 Standard Oil of Ohio domestic-style gas station plans. This homey design is often called a "house with canopy." The station was built to be leased out and initially sold Standard Oil products, but it later transitioned to Phillips 66 and then Sinclair.
In the late 1940s, with competition from nine other stations in town, O'Donnell followed the current trend, adding a two-bay garage to become a full-service station. The gas station pumped gas until the 1960s, transitioning to a body shop in the early 70s before closing in the late 1970s. The building eventually went into disrepair. After a complete restoration, the station won the National Historic Route 66 Federation Cyrus Avery Award for the year's most outstanding Route 66 preservation project in 2002. Cayuga
Meramec Caverns Barn - near North 1810 East Road on Route 66
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Located in a historic fire station and city hall, the Route 66 Association of Illinois Hall of Fame & Museum provides an excellent glimpse into the history of Illinois Route 66. Inside, you will find an impressive array of Route 66 memorabilia and vintage automotive items from across the state. It's worth spending an hour or two exploring. Make sure you venture outside to the back of the museum to see the Route 66 Mural and the mural row of Route 66 shops. Also, check out Route 66 artist Bob Waldmire’s renowned bus and van.
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Route 66 Memory Lane is a one-mile segment of the original 1926 alignment of historic Route 66. Originally Route 4, it is complete with vintage billboards and Burma Shave signs and is located just north of Lexington.
Blocked off, this segment is only driven on during parades, but feel free to stretch your legs a bit here. |
The museum building was constructed in 2022 to mimic an old Texaco service station. It is part of the attraction owing to its featured exhibit of a rare Texaco Big Friend, which towers 24 feet tall. A Mortimer Snerd Giant, also known as the Happy Half Wit, was added to the American Giants Museum in June of 2023.
There are plans to add up to five more statues to the museum grounds. Inside the Museum, visitors will find well-maintained public amenities like restrooms and rotating displays. |
The grill was named Palms, a nod to its owner's California roots. It epitomized the era's classic diner style—featuring counters with stools, square tables with four chairs each, and a slot machine for entertainment. It offered nightly dancing and chicken and steak dinners on special. The restaurant’s décor mirrored a dining spot near Adams’ former home, evoking a sense of nostalgia for a bygone era.
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After Nick Bekteshi, her husband and owner of the Country Aire Restaurant, noticed the influx of tourists visiting Atlanta's new American Giants Museum, he decided he wanted a Giant for his place, too. What better way to advertise than to celebrate his wife Lumi’s accomplishments as a prize-winning pie lady? |
The 25-foot-tall Lauterbach Giant stands on the 1926-30 alignment of historic Route 66 before Lauterbach Tire & Auto Service, proudly holding an American Flag. A nostalgic figure of yesteryear, the Paul Bunyan-designed Giant could once be found in many incarnations across America as a promotional figure dressed in his red shirt, blue pants, and weathered brown boots. He’s pure roadside Americana.
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In the early 1940s, Ed Waldmire Jr. encountered a unique sandwich called a corn dog in Muskogee, Oklahoma. This dish consisted of a wiener baked in cornbread. While he enjoyed it, Ed found that baking it took too long but struggled with a way to keep the cornbread on the wiener for quicker cooking. |
The Cozy Dog officially premiered at Lake Springfield Beach House on June 16, 1946, and later that year at the Illinois State Fair. After moving locations a few times, it settled permanently at the Cozy Drive In on Route 66 in 1949.
To this day, Cozy Dogs are made with Ed's original batter, offering a traditional cornbread taste rather than the sweeter Jiffy-like flavor often found on other corndogs. |
Motorheads is renowned for being home to the world's largest Route 66 shield and offers a unique dining experience surrounded by an extensive collection of transportation and Route 66 relics. It's more than just a restaurant; it's a nostalgic journey through Americana. |
The old drugstore has changed hands several times since the Deck family owned it. The marble top soda fountain, original hardwood floor, and shelving and showcases display old patient medicines and remedies, early equipment and fixtures, advertising, and many interesting items from years past and when the drugstore began in 1884 are all still there. |
The Litchfield Museum and Route 66 Welcome Center now sit on the property that was once Vic Suhling's Gas Station, where his eye-catching neon sign has remained for decades.
Vic Suhling first leased the property and built his gas station in 1957. By 1961, he had made enough money to finally purchase the land from the Modlin family. Vic closed the station in 1968. |
First named the Collinsville Canning and Packing Company, the Brooks brothers took over the plant in 1908 and operated it under the name Triumph Catsup and Pickle Company. Brooks sold the factory to the American Cone and Pretzel Company in 1920, and GS Suppiger Company purchased the plant in 1933.
Even though the company changed hands many times, it retained the Brooks Catsup name because it was a well-respected brand that |
About the Photographer
Susan Rissi Tregoning is the 8th photographer in the past four generations of professional photographers in her family. After a long career as an art buyer and interior designer, she put her career on hold in 2006 to travel with her husband and his job. In the process, she found her roots again, developing a photography obsession far beyond casual snapshots that evolved into a desire to capture every location and object as art. By meshing her two loves, photography and design, she has come full circle only now creating art instead of purchasing it for others.
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I am the 8th photographer in 4 generations of my family. Back in 2006, my husband accepted a job traveling, and I jumped at the chance to go with him.
I blog about long scenic drives and places that I find interesting around the United States.
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