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                                                                    EXHIBIT 10.6

                                    GUARANTY


         THIS GUARANTY (as may be amended, supplemented or otherwise modified
from time to time, the "GUARANTY") is made as of this 18th day of October, 2005
in favor of the Covered Persons (as defined herein) by Gray Television, Inc., a
Georgia corporation ("GRAY").

                                    RECITALS

         A. Triple Crown Media, Inc., a Delaware corporation ("TCM"), is a newly
formed, wholly-owned subsidiary of Gray.

         B. TCM was capitalized with $.10, and has no other assets.

         C. Gray is considering spinning off all of the shares of capital stock
of TCM to its shareholders (the "SPIN-OFF").

         D. Immediately prior to the Spin-Off, Gray would contribute
substantially all of the assets of its newspaper publishing business and
GrayLink Wireless business to TCM, and TCM would assume certain liabilities.

         E. TCM and Gray, as the sole shareholder of TCM, are considering the
merger of Bull Run Corporation, a Georgia corporation ("BULL RUN"), with and
into a wholly-owned subsidiary of TCM immediately following the Spin-Off (the
"MERGER").

         F. TCM has entered into a letter agreement in favor of the Covered
Persons (as defined herein) dated as of the date hereof pursuant to which it has
agreed to indemnify each of the Covered Person for any liabilities (including
expenses) that any of the Covered Persons may incur by reason of their status as
a proposed director of TCM (the "INDEMNITY LETTER").

         NOW, THEREFORE, to induce the Covered Persons to serve and act for TCM
and agree to be named in the Registration Statement on Form S-1/S-4 of TCM in
connection with the Spin-Off and the Merger, and in consideration of the
substantial benefit Gray will derive from the acts and service of such Covered
Persons, and other good and valuable consideration, the receipt and sufficiency
of which is hereby acknowledged, and intending to be legally bound hereby, Gray
hereby agrees as follows:

         1.01 "COVERED PERSON" means each person who has been selected as a
proposed director of TCM upon the consummation of the Merger.

         1.02 Gray irrevocably and unconditionally guarantees to the Covered
Persons the prompt, punctual and full performance of all of TCM's
indemnification and contribution obligations (including the advancement of
expenses) arising under, in accordance with and subject to, the Delaware General
Corporation Law, TCM's amended and restated certificate of incorporation, TCM's
bylaws, any resolutions of TCM's board of directors or any committee thereof, or
otherwise, as they may exist from time to time, and the Indemnity Letter, in
respect of actions or omissions by the Covered Persons occurring between
September 13, 2005 and the date on which each of the Covered Persons becomes a
director of TCM ("GUARANTEED OBLIGATIONS").

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         1.03 It shall not be necessary or required that any Covered Person
exercise any right, assert any claim or demand or enforce any remedy whatsoever
against TCM before or as a condition to the obligations of the Gray under this
Guaranty.

         1.04 Notwithstanding paragraph 1.03, Gray shall have the right to
recover from TCM for any payments made by Gray to the Covered Persons in
satisfaction of any claims against Gray under this Guaranty.

         1.05 Gray hereby acknowledges and agrees that the terms, covenants and
provisions contained in TCM's certificate of incorporation and bylaws may be
altered, modified and amended without any agreement or consent of Gray, and Gray
agrees that this Guaranty and its liabilities hereunder shall be in no way
affected, diminished or released by any such alteration, modification or
amendment.

         1.06 This Guaranty is a continuing guaranty and will remain in full
force and effect.

         1.07 Gray represents and warrants to the Covered Persons that (i) it is
a corporation duly organized, validly existing and in good standing under the
laws of the State of Georgia, (ii) it has all requisite corporate power and
authority to enter into this Guaranty, (iii) the execution and delivery of this
Guaranty and the performance by Gray of its obligations hereunder have been duly
authorized by all necessary corporate action on the part of Gray, (iv) this
Guaranty has been duly executed and delivered by Gray and (v) this Guaranty
constitutes a valid and binding obligation of Gray, in accordance with its
terms.

         1.08 No invalidity, irregularity or unenforceability of this Guaranty
shall affect, impair or be a defense to this Guaranty.

         1.09 The obligations of Gray are subject to any defenses available to
TCM (other than defenses of bankruptcy, reorganization, insolvency, moratorium
or other laws affecting the enforcement of creditors' rights generally) and Gray
is entitled to all rights of set off, counterclaims, claims for indemnity or any
other rights that may be exercised by TCM.

         1.10 No delay or failure on the part of a Covered Person to exercise
any power or right given under TCM's certificate of incorporation or bylaws or
under this Guaranty shall be a waiver and no right or remedy of a Covered Person
shall be considered abridged or modified by any course of conduct.

         1.11 This Guaranty and all claims arising hereunder shall be governed
by and construed and enforced in accordance with the laws of the State of
Delaware, without giving effect to the principals of conflicts of laws thereof.

         1.12 This Guaranty is binding upon Gray and its successors or assigns.



                            [SIGNATURE PAGE FOLLOWS.]


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         IN WITNESS WHEREOF, the undersigned hereby sign, seal and deliver this
Guaranty.


                                               GRAY TELEVISION, INC.



                                               By: /s/ Robert S. Prather, Jr.
                                                   ----------------------------
                                                   Name: Robert S. Prather, Jr.
                                                   Title: President and Chief
                                                          Operating Officer

                                               Address for Notice:
                                               Gray Television, Inc.
                                               4370 Peachtree Road, NE
                                               Atlanta, GA 30319
                                               Attn: James C. Ryan
                                               Fax: (404) 261-9607

FOR PURPOSES OF SECTION 1.04 ONLY:

TRIPLE CROWN MEDIA, INC.

By: /s/ James C. Ryan
    ----------------------------
    Name: James C. Ryan
    Title: Chief Financial Officer and Secretary

Address for Notice:
Triple Crown Media, Inc.
546 East Main Street
Lexington, KY 40508
Attn: James C. Ryan
Fax: (859) 226-4356