A Grand Tour of Cleveland – Cracking through my Hometown Travel Rut

I grew up in Cleveland, Ohio.  I carry my midwestern roots proudly and am often asked by New Yorkers I meet: “You’re not from around here right?”  Fine by me.  I try to visit Cleveland when I can, which translates to about once or twice per year.  As time is limited during these visits my first priority is to see family, friends, and dogs of family friends.  What I have neglected to see during these visits is Cleveland and all that this city has to offer.  Well that changed this weekend.

My friend Caroline, a Senior Member of the Executive Arrangements team, kindly offered to bring me on a tour of my hometown.  Our time together careening through a whole array of neighborhoods was informative and eye opening.  I could see myself living here… well almost.

Here’s some of what I learned about my hometown – Cleveland, Ohio.  I am guessing some of this intel could be news to some of it’s very residents.  We started our tour in Shaker Heights and continued East from there.  This leaves out a whole lot of the outer and completely lovely suburbs of Cleveland.  Next time.

Shaker Heights is where I grew up and where Caroline has raised her 3 children and still lives.  The homes here are beautiful, large and have gracious and well manicured front lawns.


Starter homes are also available so people can live here during all stages of life.  Sidewalks are pervasive.  And people out walking, to enjoy the leafy streets that define Shaker Heights, are prevalent.  Shaker Heights is lucky to have easy access to downtown via the Rapid Transit that runs straight through it’s environs and has done so since the 1920’s.  Taxes are high.  The schools are very good.  Restaurant choices are limited, but the Van Aken area is currently under development so hopefully things will improve on that front.

Within Shaker Heights there are 5 Lakes called:  The Shaker Lakes – man made bodies of water created by the North Union Shaker Community in the mid nineteenth century to power the mills.  The Taft Family would often head to Horseshoe Lake for our annual Christmas Card to take advantage of the fall foliage and the serene water.


All of that is still here and on Saturdays @10am the lake is home to the Shaker Pack Dog Walk starting at the Horse Shoe Lake Park Bridge.  Between 50 and 60 dogs turn up every Saturday morning for free training and some play time afterwards.  They bring their owners who also receive training.  Must check this out next time I am here.

Next stop:  Shaker Square.  Shaker Square, opened in 1929, is the second oldest outdoor shopping area in the nation.  Looking back I always thought of it as more of a circle, but the 4 quadrants do suggest a square.  On Saturdays the Square is home to an extensive Farmer’s Market and the good people of Cleveland were out in droves to take advantage of it.  We drove by the movie theater that has evolved with the times on the inside but retains it’s classic exterior.   IMG_7214

There are many restaurants to enjoy in Shaker Square.  The restaurant Fire is a favorite of many of my friends.  As is Edwin’s French Bistro.  Brandon Edwin Chrowstowski, the owner, a former inmate, started Edwins’s Leadership and Restaurant in 2007.  He hires inmates to train them to get them started in the culinary field.  Love Edwin’s.  Dewey’s Coffee looked like a cozy spot.  Eternally popular with the younger set: be sure to visit Yours Truly for some snacks and sweet treats.

img_7219.jpgWhile in the area, we also stopped by  The Nature Center.  If Shaker Square is a celebration of the social (walking, talking, shopping, and eating), then the Nature Center, some 5 minutes away from the square, is the celebration of Nature.  There are many peaceful trails to enjoy here and the space is popular for school field trips, enrichment programs and it offers an early childhood program.  In the summer there are camps.  Kids often start as campers and then return as counselors.  If you haven’t been in awhile I would recommend turning up for a stroll soon.

On to Cleveland Heights and it’s fun and funky neighborhoods.  The homes in Cleveland Heights are gorgeous.  Big and with impressive and varied architecture, it’s reason enough to spend time touring this suburb.


Taxes here are lower than Shaker Heights so you get a bit more home and land for your money.  Sidewalks are also common here and the sidewalks lead you into some fairly robust neighborhoods like Cedar/Fairmont and Coventry.     

Cedar Fairmont is independent central. With lots of little cute stores, an independent book store, and an array cute restaurants.  One could happily spend an afternoon and evening here.  Luna Bakery is said to have some wonderful baked goods and my childhood best friend’s dad’s favorite restaurant Nighttown is is still going strong (celebrating it’s 52nd year).  It is popular for it’s Jazz nights on weekends.

IMG_7222Coventry is Cleveland’s version of Haight Ashbury.  It even has the tie dyed street signs to prove it.  Ever popular with the younger set, this hood is chock full of lively and fun bars and restaurants.  Hunan on Coventry is a perennial favorite.  I am told that High Thai’d has some tasty Thai food.  Grum’s Sub Shoppe offers awesome sandwiches with surly service so be quick about your order.  Head to Big Fun for a giant and creative inventory of used and new toys.  Top that trip off with a visit to Piccadilly for organic/vegan frozen yogurt.  Hmm…

img_7224.jpgLittle Italy 
 By this time I was starving so driving through Little Italy without stopping at each and every inviting old school restaurant was challenging.  Caroline was focused!

Our tour through here reminded me of the Arthur Avenue area in the Bronx, my new favorite lunch spot after a visit to the Botanical Gardens.  As Cleveland’s Little Italy is about 10 minutes from the Cleveland Botanical Garden, I could easily see a field trip like this in my Cleveland future.  The story with Cleveland’s Little Italy is that Italian sculptors came to work on the Lake View cemetery and some downtown buildings and stayed.  Now there are also quite a few art galleries to visit in between eating.


Head to Mama Santa for cheap, but awesome pizza and any of the restaurants I spied through my window looked like home runs to me.  It also looks quite livable and the streets were filled with people milling around on their Saturday.  Graduate students are drawn to this neighborhood as they can walk to Case Western Reserve University and the hospital.  Little Italy is home to Rising Star, Cleveland’s most favorite home grown coffee shop.  To hang your hat for a bit in Little Italy you can stay and eat in the Washington Place Bistro and Inn.  Fun!  Get thee to Little Italy.

Onward to Uptown.  This area bubbled up in the last five years to better service the ever growing student body that is turning up in Cleveland.  On the edge of University Circle, this scrappy little bastion offers an array of entertainment ideal for the student to explore when not pursuing their studies.  Uptown is considered the “main street” of University Circle though the actual street name is Euclid Avenue.  Definitely worth a pop by before or after you make your way around University Circle.

University Circle and/or Cleveland’s Cultural Hub and as it’s website lists:  “Ohio’s Most Spectacular Square Mile.”  I never realized it is just one square mile and if this is the case it is really impressive what they have packed into this plot of land.  The crown jewel in the collection is The Cleveland Museum of Art.  About 5 years ago this, always a pleasure to visit museum, received an extensive multimillion dollar expansion.  The approach to this museum and surrounding natural space is impressive and concomitant with the art collected inside.


The second pretty major feather in University Circle’s cap is Severance Hall, the winter home to The Cleveland Orchestra.  Also within the square mile is the Cleveland Botanical Garden.  At the center of this enclave of Eds, Meds and Arts is Wade Oval.  University Circle Inc. offers concerts every Wednesday in the summer and sets up an ice rink on it in the winter.  There is the Western Reserve Historical Society and the Cleveland Museum of Natural History which includes an outdoor wildlife area for animals who cannot survive in the wild.

IMG_7229I loved our meandering drive through the tranquil and really quite expansive LakeView Cemetery – final resting place to the who’s who of Cleveland including: James Garfield,  Elliot Ness, John D. Rockefeller’s and some Tafts.  I know a cemetery seems an odd choice to grab your group and go, but this one is well worth your time.

The cemetery offers walking tours and an array of classes on site that offer theme based learning.  We popped into the chapel that honors Jeptha Wade the founder of Western Union, who donated the land where Wade Oval and museums all sit and one of the founders of the Cemetery.  His son built the chapel in his honor and went to Tiffany’s in NYC to have the spectacular stain glass window designed custom for his father.


As we made our way downtown Caroline was rightfully proud to point out the Cultural Gardens (that I had never heard of). These plots of land were donated by John D. Rockefeller to ensure that green space was maintained as one approached the city of Cleveland.  Each patch of land is owned and operated by a cultural institution that uses the land to show off their culture.  They are all Peace Gardens and many are two-tiered, such as the gardens maintained by Germany and Italy.  What a lovely idea and fun to open my eyes to a part of the city that I had driven through a million times, but never once stopped to consider.  There is a bike path here that would be the ideal way to admire the gardens. It goes all of the way to Lake Erie.  Must return and do that.

Downtown/Warehouse District By this point I was wondering if Caroline was ever going to stop for food.  My girl has stamina!  She also has empathy as I think she could sense my gradual denouement in energy.  So we did a quick spin through Downtown where she pointed out the warehouse district – the first area allocated for lodging Downtown.  These buildings were converted from old warehouses used by the garment industry.  The Bingham and The Archer are the best addresses in town and it can be competitive to acquire an apartment in either one of them.  This New Yorker eyes nearly popped out of her head when she looked at the rental price points.   Best not to dwell on that.  I also spied a Heinen’s – the grocery store of my childhood – so these downtown folks do have access to groceries.  Located in the restored Cleveland Trust Bank building it is one of the more fancy Heinen’s I’ve seen complete with Tiffany glass windows in it’s impressive dome.   What is it with Cleveland and Tiffany glass?

She showed off the shiny new Hilton that was built in advance of the Republican Convention.  This new entry into the downtown Hotel line up offers a swanky spot for cocktails on the 32nd floor and direct underground access to the Convention Center.  It is also two blocks from the Rock and Roll Hall of Fame.  Other hotels worth considering are the Kimpton, Westin, Drury, Ritz Carlton and the Renaissance,  most with easy access to Tower City (an indoor shopping mall).

IMG_7238.jpgThe quick spin through downtown was necessary for us to get to Ohio City just over the bridge and across from downtown and home to FOOD.  Lots and lots of food and happily my lunch.  After some serious hunting for a parking spot we made our way to the West Side Market.

The West Side Market is a big beautiful food hall that is almost 100 years old.  Sprouted up around it are restaurants, a glass blowing studio, and breweries – 7 breweries in fact!  This area is also home to the largest urban farm in the city of Cleveland and they have a storefront that abuts the garden to sell their hot out of the dirt products.

The West Side Market was JAM PACKED with people filling their baskets with all sorts of foodie treasures.


It was a feast for my eyes and torture for my grumbling stomach to walk through all of these delectables, but Caroline had a destination in mind: The Crepe Place.  Oh happy day, lunch!  There was bit of a line, but it was fun to watch the crepes slowly being assembled.  And I got to witness the one non-friendly Ohio person: The Crepe Lady.  We COULD NOT get her to crack a smile.  Maybe she is from NYC?  Kidding.  But she makes a mean crepe to match her less than sunny exterior.  We headed to the second floor for an awesome view of the West Side Market hustle and bustle as we devoured our spinach, tomato, and goat cheese crepes.  Satiated we continued our tour.


Gordon Square Art District Located on the near west side of Cleveland, has become home to several theaters: Cleveland Public Theater, Near West Theater and the Capital Theater (part of Cleveland Cinemas).  The area also includes the 78th Street Studios, independent shops (Fount from the Cleveland Flea and LeBron James’ Cleveland Hustle television show fame) and restaurants including the Happy Dog, Sweet Moses and Spice. New lakefront housing that offers Lake Erie views and beach access through Edgewater Park can also be found here: The Shoreway, The Edison at Gordon Square and Battery Park to name a few.

Gordon Square sponsors an Artist network open to any artist or creative professional who lives and works in the neighborhood — emerging network of artists, musicians, actors, poets, designers, photographers, etc.  It is a great place to catch a show, grab a meal or spend the afternoon.  If I was 28 and moving to Cleveland this and the downtown warehouse districts are definitely areas I would seriously consider.

Edgewater Park and Beach Formerly a State run park, it is now part of the award winning Cleveland Metroparks.  The 240 acres that include Edgewater Beach, Marina and Yacht Club, features 9000 feet of shoreline, dog and swim beaches with lifeguards in the summer, boat ramps, fishing pier, picnic areas with grills and a rentable pavilion.  We stopped in the upper part of the park for some of the most stunning views of downtown Cleveland and a photo op with one of the famous “Cleveland” signs.  And check out that beach!!!     The beach is easily accessed through a tunnel from Battery Park.   City living with a water feature – bonus!


Playhouse Square This theater geek was surprised to learn that Cleveland houses the SECOND largest theater hub outside of – you know where – NYC.  I had no idea! And what a facility it is.  Beautiful soaring ceilings and multiple theaters with all sorts of stages to accommodate all sorts of productions.  We snuck into the theater where Waitress: The Musical was just finishing up it’s matinee performance.  The theater was 94% filled at showtime and the audience walked out beaming and energized.  We even checked out the bathrooms – many a NYC theater would be jealous of the restroom set up at Playhouse Square.  Cleveland is a Tier One city which means it is at the head of the line to receive Broadway traveling productions.  Hamilton is arriving in the spring!  Someone could easily set up a theater club here to take advantage of the rich and varied array of entertainment offerings here.

Playhouse Square offers a Broadway Series where you can buy a package that includes all seven shows in the line up on your chosen night.  They make it easy to swap nights and offer a very appealing range of pricing.  One can buy a series that averages to $78 per show or as low as $21 a show, making the arts accessible to as many people as possible.  Cleveland friends – if you have not see Waitress I would HIGHLY recommend it for a fun evening out. It is closing: Sunday, November 5th.  And would also put a plug in for The Humans a 90 minute play that scored the Tony for Best Play in 2016 arriving in April.

Some final observations: ?? Cleveland is a small city with a whole lot of heart.  With the exception of the Crepe Lady, most everyone we encountered on our tour was personable, warm, and well mannered.  The midwest vibe is alive and well and on display in Cleveland.  Even the dogs were a bit more friendly than they are in NYC! Cleveland folks are thirsty.  Lots and lots of microbreweries and places for general consumption of libations abound.


Cleveland is not a taxi town.  Uber is the name of the game here or you drive and someone abstains.  There are quite a few pleasant neighborhoods that offer pleasant walk to town experiences, but if you want to travel from town to town it will be via four wheels.  Cleveland is committed to it’s sport teams and it’s culture.  I made little mention the Rock and Roll Hall of Fame, but it is a reason to visit this city and drives a great deal of tourist traffic for this town.  I just hope these visitors are making the most of their visit when they are there.

I was and will always be proud to be from Cleveland and it makes me happy to have seen in it in such a vibrant state.  I will have to visit more often to take full advantage of it.  You should grab your group and go too!



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Space does open up! When it does it’s often at the last minute. Will keep our fingers crossed. Would love to see you at this experience!