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April 17, 2019

Supplement to Prospectus and Summary Prospectus each dated April 30, 2018, as amended.

At a meeting held on April 15, 2019, the Board of Directors (the "Board") of Wintergreen Fund, Inc. (the "Fund") approved the liquidation and dissolution of the Fund. Effective immediately at market close on April 17, 2019, the Fund has suspended most sales of its shares pending the completion of the liquidation and the payment of liquidating distributions to its shareholders. The Fund expects to make the liquidating distributions and cease operations on or shortly after June 3, 2019 (the "Liquidation Date").

In limited circumstances, such as sales to certain retirement plans and sales made through retail omnibus platforms, the Fund will continue to offer its shares for a limited time, but no offer or sale of Fund shares will be made after April 30, 2019.

Shareholders should be aware that the Fund will convert its assets to cash and/or cash equivalents before the liquidating distributions are made to shareholders. After the Fund converts its assets to cash, the Fund will no longer pursue its stated investment objective or engage in any business activities except for the purposes of winding up its business and affairs, preserving the value of its assets, paying its liabilities, and distributing its remaining assets to shareholders.

In connection with the liquidation, the Board approved the immediate suspension of the Fund's distribution and/or service (Rule 12b-1) fees. The Board also approved a waiver of the redemption fee of 2.00% imposed on shares redeemed within 60 days of purchase for redemptions of Fund shares that occur after the date of this supplement.

If a shareholder has not redeemed his or her shares prior to May 30, 2019, then the shareholder's account will be automatically redeemed and proceeds will be sent to the shareholder's address of record.

The liquidation of the Fund, like any redemption of Fund shares, will constitute an event upon which a gain or loss may be recognized for state and federal income tax purposes, depending on the type of account and the adjusted cost basis of the investor's shares. The tax year for the Fund will end on the Liquidation Date.

The Fund expects to make one or more distributions of income and/or net capital gains prior to the Liquidation Date in order to eliminate Fund-level taxes. The Fund must declare and distribute to shareholders realized capital gains, if any, and all net investment income no later than the final liquidation distribution. The Fund currently expects to pay a capital gains distribution prior to the liquidation of the Fund. As with any other distribution, such pre-liquidation distribution by the Fund will be taxable unless you hold shares in a tax-advantaged account, such as an IRA or a retirement plan.

Please contact your tax advisor to discuss the tax consequences to you of the liquidation.

Important Action Required for Direct Shareholders with IRA Accounts

As an IRA account shareholder holding an account directly with the Fund, you should contact a shareholder service representative at 1-888-468-6473 to arrange a transfer of your Fund assets to another IRA custodian.

Please respond by May 30, 2019. If we do not receive a response by May 30, 2019, your investment in the Fund will be liquidated as an age-based distribution with 10% federal withholding on the Liquidation Date. Please also note that state withholding may also apply. Checks will be mailed to your address of record. You may have a limited time, typically 60 days, to reinvest proceeds to avoid tax consequences.

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The Fund is subject to several risks, any of which could cause an investor to lose money. The Fund may purchase risk arbitrage securities (securities of companies involved in a restructuring) or distressed companies. These companies may not be successful in their restructuring and securities of distressed companies are generally more likely to become worthless than securities of more financially stable companies. Smaller companies involve substantial risk as these securities are traditionally more volatile in price than larger company securities. Value risk is that the securities in which the Fund invests may never reach what the Investment Manager believes are their full market values. Securities rated below investment grade, sometimes called junk bonds, involve a greater degree of risk than investment grade bonds in return for higher yield potential. The Fund may be subject to interest rate risk which is the risk that debt securities in the Fund's portfolio will decline in value because of increases in market interest rates. By participating in derivative securities, the Fund may attempt to hedge (protect) against currency risk which is the risk that the value of foreign securities may be affected by changes in currency exchange rates. Derivatives can be volatile and involve various types and degrees of risks, depending upon the characteristics of a particular derivative. International investing involves certain risks and increased volatility not associated with investing solely in the U.S. These risks include currency fluctuations, economic or financial instability, lack of timely or reliable financial information or unfavorable political or legal developments. These risks are magnified in emerging markets. As a result of appreciation of certain of the Fund's portfolio securities and/or a change in the size of the Fund, investments in a particular sector or industry may represent a significant portion of the Fund's overall portfolio. If this occurs, the Fund will be subject to greater potential risk than funds that do not have as much exposure to such sector or industry. Short sale risk is the risk that the Fund will incur an unlimited loss if the price of a security sold short increases between the time of the short sale and the time the Fund replaces the borrowed security.

In light of these risks, the Fund may not be suitable for all investors.

Before investing you should carefully consider the Fund's investment objectives, risks, charges and expenses. The prospectus and summary prospectus contain this and additional information regarding the Fund. To obtain a prospectus or summary prospectus, please download from this site or call toll-free 1-888-468-6473. The prospectus and summary prospectus should be read carefully before investing. This website is not a solicitation for the Fund outside of the United States.

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