A Spanish land grant at the turn of the 19th century made to Joseph Keiffer and used for farming by G. Gratiot included part of the area that is now the Castlewood community and that part of Castlewood State Park lying north of the Meramec River. From that time, a parcels of the property passed through many ownerships: Nicholas Dresdehan, Alexander Andre, L.E. Strothkamp, St. Paul Lime Company, Ranken Estate, Union Sand and Gravel Company, and the Meramec Realty Company. The name "Castlewood" is probably derived from "Castle Woods," an unsuccessful speculative subdivision development in 1871 along the bluffs just west of the present community.
Castlewood flourished as a resort between the First and Second World Wars. In 1915, the Meramec Realty Company developed a recreational area with 250 clubhouses, hotels, stores, boathouses, and bath houses. "Castlewood on the Meramec River ... the very name implies recreation ... the thought alone spells the words play, resort, and beauty," boasted their advertisements. Visitors from the city came by the thousands. Most rode the Missouri-Pacific Railroad along the north side of the river to the Fern Glen, Mountain Ridge, and Castlewood depots, or on the Frisco Railroad along the south side to Morschels and Deicke. The crowded train rides themselves began and ended the weekend merriment with camaraderie and singing. Some took the streetcar to the end of the line at Meramec Highlands, now the west end of Kirkwood, from which they would walk seven miles along the tracks. Others drove out in early model cars, patching tires as they came.
Days were spent enjoying canoeing, horseback riding, badminton, corkball, indoor ball (softball), horseshoes, sunbathing, and swimming. Thousands of the bathers would gather at Lincoln Beach, arriving by canoes and small boats from up and down the river. This popular beach was a byproduct of earlier dredging by the Union Sand and Gravel Company, which operated a separating plant from aggregate on the east bend of the river. Nights offered dancing at local dance halls, or parties and skits put on by members of the clubhouses, and of course, drinking home brew! "Every day was a picnic, every night was a party." During Prohibition, from 1918 to 1933, in the privacy of the clubs, batches of home brew were " ... set up on Sunday night, bottled on Wednesday, iced on Friday, and drunk on the weekend."
While some families and many bachelor groups owned or leased clubs, giving them such names as "Happy Hollow," "Wigwam," "Stallions," "Gin Creek," and "Nuthatch,' many young women stayed in the dormitories of the Wagner Electric Girls Club and the Catholic Corona Club. The church of the club for years held Mass on summer Sundays for hundreds of weekenders. Rooms also were available at the Washington and Jefferson, both five-story hotels, Lincoln Lodge, the Castlewood Hotel, and the Halls Store. Wide concrete steps, now deteriorated and overgrown, lead from the bluff top down to the Castlewood Depot shelter and the U.S. Post Office at Halls Store. Huge barns along the river housed and rented hundreds of canoes. Much of the fresh produce and meat enjoyed was provided by local farmers.
With the end of prohibition came the beginning of the tavern business. A various times, as many as ten taverns lined the streets. Weekend patrons strolled from tavern to tavern; The Trees, Blind Kelly's, Castlewood Bar, Red Dog Saloon, Bill Breits, Castlebar, Crossroads, Halls Tavern, and The Lone Wolf Club. The only licenses granted by the state in unincorporated areas were for 3.2 beer, but most taverns "pitched liquor" and stayed open on Sunday, Some played "bingo trees" and had nickel and quarter slot machines "owned by the syndicate" which gave cuts to the tavern owners. Timely telephone calls would usually protect tavern owners from the law. Hotels, taverns, and dance floors on the banks of the Meramec attracted noted musicians such as Russ David, Charlie Creeth, Leonard Breit, Earl LaBoube, and Carl Stermer. The Castlewood Pool, a half-moon shaped 18,000 square foot spring-fed pool, was designed by Ray Woods, a nationally known highdiver, in the early 1940's. The pool at first rivaled Lincoln Beach, but later replaced it as the sandy beach became less popular and overgrown.
After World War II Castlewood gradually became a residential community. Better means of transportation made points further southwest more accessible for recreation. The hotels and many of the clubs burned, and those remaining were either torn down or renovated for year round living. Most of the taverns were converted to other uses, among them a grocery store, apartments, and a church.