My mum had a blue Handspring Visor, which was great for playing Bejeweled on long car journeys in 1999! At the time I used a personal organiser from Time Magazine to note down homework assignments.

In 2006, a friend at my parent's Bible study group donated an regionalised HTC Himalaya (Orange SPV M1000) running Windows Mobile 5. It was so powerful! My favourite was pPod, an iPod emulator. It could also run MSN messenger, and even though it needed a separate SDIO WiFi card to connect, it was possible continue chatting to a certain girl in California even after my bedtime XD

Is there a place like MacintoshGarden/MacintoshRepository/WinWorldPC for old Pocket PC or Palm apps? I've got a small collection (Pocket PC below):

Accessories: bkpmgr, btaudio.cab, cryptainer_le.arm.CAB, FinchSync.CAB, G7B0Keybd.ARM, GMobileSyncSetup.CAB, iPAQFoldableKeybd.ARM, Keyboard Driver.PPC300_2577.cab, NETCFv2.wm.armv4i.cab, OggSync.CAB, PocketTV.POCKETPC_ARM_POCKETGEAR_2000.CAB, SpbBackup.arm, SPB Keyboard Serial, SpbFullScreenKeyboard3.arm.cab, Stowaway Keyboard Driver.PPC300_2577.cab, Sunnysoft_BackupManager_3766_EN_build_08091.CAB, Webby200.cab, WiFiTunes.CAB, wlan11b-etsi.cab, FreqTune15setupARMSR1.EXE, PPCV16, Sunnysoft_BackupManager_3766_EN.exe
Communications: AgileMessengerWMPPC.CAB, gizmo.jar, MinimoCE_0.016.cab, msn_2002.CAB, msn_2003.CAB, SJphone-PPC2003SE-303c.cab, SkypeForPocketPC_Beta.CAB
Emulators, Control: AppleCE, Clicker_PocketPC_5.CAB, Mini vMac Plus, Mini vMac SE, Palm, PGPwireless for WinCE Desktop Integration, PocketIIe.PPC_ARM.CAB, PocketPuTTY.exe, pocketVNC.exe, ppcconnector.exe, RACtrlCE.cab, Remote Keyboard, rkb.PPC_ARM.CAB, Salling Clicker for Pocket PC.CAB, StyleTapDevice.cab, StyleTapDevice11003.CAB, ti83 Plus v1.03.rom, TIPocketEmulator.CAB, VNCVIEW.EXE, BibleReader_365_108, pPod, rkbsetup.exe, StyleTapSetup09150.exe, vti
Factual Recall: BPeST_PPC.ARMV4.CAB, BPeST.cab, ConverterCE.ppc30_arm.CAB, lexipedia.cab, MxConv.PPC_ARM.CAB, OED, Pocket E-Sword, PocketXpdf_0.4.0.CAB, TomeRaider, Translator, BeSt, Bibles to Pocket PC, esword ppc2003setup252.exe, GNB.EXE, Pocket Oxford English Dictionary and MSDict Viewer PPC_5.10.43PG.exe, PocketOxfordEnglishDictionaryandMSDictViewerPPC_5.10.43.exe
Games: AirHockeyinstall.Arm.CAB, AOE, Bejeweled-arm.exe, bejeweled-ppc-v2-51.cab, Chess_PPC.ARM.CAB, FreaK.arm.cab, GemSwap_PPC.CAB, Kevtris.CAB, pacman.PPC_ARM.CAB, PPcReversi.ARM.CAB, reversi_ppc, AOE, GemSwapPPC.exe, PacMan.exe
Maps: BSGPSPDA.CAB, california.osm.bz2, CartoExploreur3CE.CAB, gmapsupp.img, GoogleMaps.CAB, GPS Speedo.exe, gpsed.ppc.cab, GPSGate, GpsPortPPC.exe, GPSTuner_v5.CAB, GPSViewer, gpsVPppc, MapAlive, mgmaps_wm, mgmaps-signed.jad, mgmaps.jad, MMPocketNav.PPC2K_ARM.CAB, MuskokaTech PathAway GPS 4.CAB, PathAway GPS 4 for Windows Mobile, PathAwayInstall.cab, Pocket Atlas-arm.arm.CAB, TomTom Taiwan, ptgmap_1
Multimedia: flash player 7_ppc_en.cab, JB_Piano.ARM.CAB, mobiolawebcam_3_1_8_wl_wm, pPod, SoftMaker Office 2006, tcpmp.pocketpc.0.72RC1.cab, vlc-0.8.5-svn-20060214-0130, VTSoundEditor, ofpw08beta.exe, PMPW04EV.EXE, pmpw06beta.exe, smcw06dict.exe, Softmaker Office 2008, Softmaker Trial Installer ofpw06ev.exe
System: ActiveXPack1.PPC_ARM.CAB, CapSure.CAB, Cloudyfa_EsmertecJbed.cab, ExportContacts setup.CAB, Jbed-WM2003 Folder, mbutton.PPC_ARM.CAB, regedit.Mrln_ARM.CAB, SMS Export.cab, Ultimate Theft Alert v35 FULL with GPS and MONITOR Plugin, EZ150PPE.EXE, NETCFSetupv2.msi, Pocket PC WiFi
Themes: Crossbow.tsk, iPhone Theme, Slide2UnLock1.19-WM5.cab
Other: gps_tuner_5.1_code.exe, Missing_Sync_for_Windows_Mobile.app.zip, missing_sync_winmobile4.0.2.dmg, Softmaker Office, SPB Full Screen Keyboard, Taipei MGMaps, TomeRaider, TomTom, TT6 Navigator and Go, Unlocking, WM Memory Card, WM5 English