I've lived in many places and recently two years of it was in Cleveland. You can't say much positive about Cleveland, but they do have their bike act down.
There are rides most every weekend in Northern Ohio.
http://www.ohiocycling.info/OBEC.html
The 100-mile Emerald Necklace sets a standard for any city to emulate. The Emerald Necklace is a connecting park system around the city.
Rock Creek Park was always my favorite Sunday ride.
The Tow Path National Historic site is world class, and they're lucky to have it (I know this crowd isn't into paths, but my family rode our tandem with trailer bike there). Much history.
http://www.nps.gov/archive/cuva/plan...n/ohioerie.htm
The area has many organized rides ie the Sweet Corn Ride in July. All through the Amish countryside.
http://www.sweetcornride.com/
THIS AREA IS A BIKING CLASS ACT!!!!!!!!!
The local shops:
Best road bikes in Cleveland are found at The Bike Authority in Broadview Heights (South side).
http://www.bikeauthority.com/ Talk with Sherman. He's hands on and knows his business. The only shop in town that spoke to me about fitting. They measured me. Used a computer and some other apparatuses. I bought a CAAD 7 from them.
B & K Bike Shop in South Euclid (East side) has been there for several decades. Family run and the owner is always there. Very competent. I bought a Burley Piccolo from them.
http://www.bandkbike.com/
Century Cycles has a knowledgeable staff too (many locations around the city). High-end road bikes are not their forte. One of their shops is on the Tow Path. I bought a Burley tandem from them.
http://centurycycles.com/index.cfm
Eddy's is the big shop in the area. At their main store in Stow they have a few associates that know bikes. Most of their hired help know less than I do, and I don't know much.
http://eddys.com/index.cfm
Hub Bub is a great store too with great knowledge on all bikes and tandems (custom too). I think they head the National Tandem Society.
http://www.hubbub.com/