Clue is a Windows application to create and print control description sheets for orienteering events. NEOC has a club license. Clue is available via the DVOA website.

Note: Purple Pen can print cluesheets that are associated with a course.

Course-setting software for Windows with features for loops, butterflies, forks, relays, etc. Draw courses on an OCAD map; output to .pdf.
The "light" version is free (max. 2 courses, 25 controls).

Utility that enables any Windows program to "print" to a .pdf file. Make a .pdf of your clue sheets, then take those files to the print shop.

Notes: 

• The current version of PurplePen can output "coursed" maps in .pdf format directly, but you'll need CutePDF (or similar) to output separate cluesheets.
• Windows 10 includes "Microsoft Print to PDF" which makes utilities like CutePDF unnecessary. In the Print dialog, click the "Name" drop-down and choose "Microsoft Print to PDF."

Cartography drawing program, for Windows. Can be used for course-setting. Free trial version works for 21 days, limited functionality.

The free OCAD Viewer can export OCAD maps in .pdf format.

Free meet-management software. Reads SportIdent dibbers to produce meet results and splits files. Runs in simulation mode on any Java machine; requires Windows (and SI driver) to read from dibber download box.

Utility that enables any Windows program to "print" to a .pdf file. Make a .pdf of your clue sheets, then take those files to the print shop.

Notes: 

• On installation, it will prompt you for name and email address. These are not required.
• See the Notes to CutePDF above. Same info applies about Purple Pen and Windows 10.

Free course-setting software, for Windows XP and later. Excellent built-in Help.
Draw O-courses on a .pdf or .ocd map file; add control descriptions and text. Can output .pdf files for the print shop. Can generate files for Route Gadget.