I recently had reason to upload a lot of files to Sharepoint 2010. Unfortunately the Upload item in the menu would only allow me to do this in batches of 100.  Fortunately however, you can do this from code.

    Public Function UploadToSharepoint(ByVal localFile As String, ByVal remoteFilename As String, spUrl As String, username As String, password As String, domain As String) As Byte()

        ' Ensure that we've got a valid URL.
        If Not spUrl.EndsWith("/") Then spUrl &= "/"

        ' Build the remote url, escape spaces and replace backslashes.
        Dim rfURL As String = String.Format("{0}{1}", spUrl, remoteFilename).Replace(" ", "%20").Replace("\", "/")

        ' Create a webclient.
        Dim wc As New WebClient
        wc.Credentials = New System.Net.NetworkCredential(username, password, domain)

        ' Attempt the upload.
        Try
            Using s As New System.IO.FileStream(localFile, IO.FileMode.Open, IO.FileAccess.Read)
                Using reader As New System.IO.BinaryReader(s)
                    UploadToSharepoint = wc.UploadData(rfURL, "PUT", reader.ReadBytes(CInt(s.Length)))
                End Using
            End Using

        Catch ex As Exception
            UploadToSharepoint = Nothing

        End Try

    End Function