Under Construction. Lake Wales, named after Lake Wailes, is a small but growing historical city in the Lakeland-Winter Haven Corridor and perfectly positioned between Orlando and Tampa. Downtown Lake Wales is a historical destination and is well known as Florida’s first Main Street Program. Now home to everyday business, boutique shopping, coffee shops, and delicious local restaurants. On Saturdays, find the local farmers market bustling from 9-1pm at the downtown marketplace. Head out to Lake Wailes and check out the 2.5-mile biking/hiking trail or take a seat on the pier and enjoy a nice picnic overlooking the water. Don’t forget to take a quick drive over to Spook Hill to see for yourself if the tales that have been told here for decades are true.