diff --git a/README.md b/README.md
index e090c8a..7bebcce 100644
--- a/README.md
+++ b/README.md
@@ -93,4 +93,5 @@ The following options can be set in `/etc/molly.conf`:
   all intermediate directories must exist, Molly Brown won't create
   them for you.
 * `DirectorySort`: A string specifying how to sort files in automatically generated directory listings.  Must be one of "Name", "Size" or "Time" (default value "Name").
-* `DirectoryReverse`: Boolean, if true automatically generated directory listings will list files in descending order of whatever `DirectorySort` is set to (default value false).
+* `DirectoryReverse` (boolean): if true, automatically generated directory listings will list files in descending order of whatever `DirectorySort` is set to (default value false).
+* `DirectoryTitles` (boolean): if true, automatically generated directory listings will use the first top-level heading (i.e. line beginning with "# ") in files with an extension of `GeminiExt` instead of the filename (default value false).
diff --git a/config.go b/config.go
index 49f7dfe..99d2efe 100644
--- a/config.go
+++ b/config.go
@@ -21,6 +21,7 @@ type Config struct {
 	SCGIPaths        map[string]string
 	DirectorySort    string
 	DirectoryReverse bool
+	DirectoryTitles  bool
 }
 
 type MollyFile struct {
diff --git a/handler.go b/handler.go
index f0886ec..7c07ff0 100644
--- a/handler.go
+++ b/handler.go
@@ -312,12 +312,12 @@ func generateDirectoryListing(URL *url.URL, path string, config Config) string {
 		if uint64(file.Mode().Perm())&0444 != 0444 {
 			continue
 		}
-		listing += fmt.Sprintf("=> %s %s\n", url.PathEscape(file.Name()), generatePrettyFileLabel(file))
+		listing += fmt.Sprintf("=> %s %s\n", url.PathEscape(file.Name()), generatePrettyFileLabel(file, path, config))
 	}
 	return listing
 }
 
-func generatePrettyFileLabel(info os.FileInfo) string {
+func generatePrettyFileLabel(info os.FileInfo, path string, config Config) string {
 	var size string
 	if info.IsDir() {
 		size = "        "
@@ -335,11 +335,12 @@ func generatePrettyFileLabel(info os.FileInfo) string {
 		size = "GIGANTIC"
 	}
 
-	var name string
-	if len(info.Name()) > 40 {
+	name := info.Name()
+	if config.DirectoryTitles && filepath.Ext(name) == "."+config.GeminiExt {
+		name = readHeading(path, info)
+	}
+	if len(name) > 40 {
 		name = info.Name()[:36] + "..."
-	} else {
-		name = info.Name()
 	}
 	if info.IsDir() {
 		name += "/"
@@ -347,6 +348,24 @@ func generatePrettyFileLabel(info os.FileInfo) string {
 	return fmt.Sprintf("%-40s    %s   %v", name, size, info.ModTime().Format("Jan _2 2006"))
 }
 
+func readHeading(path string, info os.FileInfo) string {
+	filePath := filepath.Join(path, info.Name())
+	file, err := os.Open(filePath)
+	if err != nil {
+		return info.Name()
+	}
+	defer file.Close()
+
+	scanner := bufio.NewScanner(file)
+	for scanner.Scan() {
+		line := scanner.Text()
+		if strings.HasPrefix(line, "# ") {
+			return strings.TrimSpace(line[1:])
+		}
+	}
+	return info.Name()
+}
+
 func serveFile(path string, log *LogEntry, conn net.Conn, config Config) {
 	// Get MIME type of files
 	ext := filepath.Ext(path)