March 28, Dear Valued Customer:

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1 March 28, 2018 Dear Valued Customer: We are pleased to announce that Bay Bank is merging with Old Line Bank to become the premier community bank in the state of Maryland. The Bay Bank branches will open for business under the Old Line Bank name on April 14, Old Line Bank, a Maryland-based bank, was founded in 1989 in Waldorf, Maryland. Since that time, the Bank has charted a path of steady growth and now has 28 branch locations serving 9 Maryland counties. We are proud to share that by combining our organizations, Old Line Bank will become the third-largest independent commercial bank based in Maryland, with assets of more than $2.8 billion and 37 full service branches serving Anne Arundel, Baltimore, Baltimore City, Calvert, Carroll, Charles, Frederick, Harford, Howard, Montgomery, Prince George s and St. Mary s Counties. The combined Bank will have the second-most banking locations of all independent Maryland-based commercial banks. Old Line Bank is categorized by regulators as being well-capitalized and has a solid history of sound business practices. Old Line Bancshares, Inc., the parent company of Old Line Bank, is publicly traded on the NASDAQ Capital Market under the symbol OLBK. This transaction will benefit customers of both Bay Bank and Old Line Bank, as well as the shareholders of both Bay Bancorp, Inc., the parent company of Bay Bank, and Old Line Bancshares, Inc. Through the process of bringing the two banks together, our goal is to facilitate a smooth transition and allow customers to continue to perform banking transactions as normal. Please review the enclosed Frequently Asked Questions document for additional information regarding the merger and if you have any questions, please contact your local Bay Bank representative. After the branches have been rebranded with the Old Line Bank name and logo, you will continue to see the same friendly and familiar faces that you ve grown accustomed to servicing all of your financial needs. We are committed to providing the most convenient banking services with superior personal attention to all of our customers, and we look forward to welcoming you to Old Line Bank. Sincerely, Joseph J. Thomas President and Chief Executive Officer Bay Bank James W. Cornelsen President and Chief Executive Officer Old Line Bank

2 Old Line Bank and Bay Bank Merger Frequently Asked Questions Why is Bay Bank merging with Old Line Bank? Both Bay Bank and Old Line Bank are strong local financial institutions that provide personal, one-on-one service to customers in the state of Maryland. By merging the two organizations, Bay Bank customers will gain additional products and services, as well as access to 26 full service branches across nine Maryland counties. Has the merger received all required approvals? Yes, the transaction has been approved by the proper regulatory agencies and the shareholders of both Old Line Bancshares, Inc. and Bay Bancorp, Inc. The Bay Bank branches will open for business as Old Line Bank on April 14, Will Bay Bank change its name? Yes, under the terms of the merger agreement, the name will change to Old Line Bank. When will I notice the new signs? On April 14, 2018, you will see the Old Line Bank signs installed at all Bay Bank branches. Who is Old Line Bank? Old Line Bank is a Maryland-based bank headquartered in Bowie, Maryland. Old Line Bank was founded in 1989 in Waldorf, Maryland. Since that time, Old Line Bank has charted a path of steady growth with 28 branch locations serving nine counties. Old Line Bancshares, Inc., the parent company of Old Line Bank, is publicly traded on the NASDAQ Capital Market under the symbol OLBK. Old Line Bank s mission is to promote the growth and prosperity of the communities we serve. Our strategic plan is built on the premise of enhancing shareholder value and growth through branching and operating profits. Why the name Old Line Bank? The State of Maryland earned her nickname the Old Line State in 1776 during the first major battle of the Revolutionary War. The war could have ended that day had it not been for the Maryland 400, who after General George Washington ordered a retreat, sacrificed themselves, allowing the Continental Army to escape. Maryland s regiment of soldiers referred to as the Old Line achieved a reputation as saviors of the Continental Army and the cause of independence. As a tribute to the contributions and heroic sacrifices of those brave Maryland men, Old Line Bank proudly chose its name.

3 What happens now with my Bay Bank account? Nothing at this point, it is business as usual. You may continue to conduct your banking as you always have. We plan to integrate the operating systems of both banks on June 1, Will the bank name on my statements and Online Banking screens change on April 14, 2018? No, you will continue to see the Bay Bank name on your statements and many of the Online Banking screens until the integration of the bank operating systems on June 1, After the systems have been integrated on June 1, 2018, all statements and Online Banking products will say Old Line Bank. Will my Bay Bank branch be closed? No, all Bay Bank branch locations will remain open. More importantly, you will continue to see the same friendly staff at each branch. Old Line Bank is excited to expand its footprint to include Baltimore City, Howard and Harford Counties and add to our branch network in Anne Arundel and Baltimore Counties. Will branch hours change? Most branch hours will remain the same. You may see some minor adjustments to enhance hours. Can I continue to use my Online Banking and Bill Pay? Yes, on April 14, 2018 the Bay Bank website will be re-directed to Old Line Bank. You will see a Welcome Bay Bank Customers landing page with the most up to date merger highlights. Login to your Online Banking by simply clicking the Online Banking Login button on the upper right hand side of the browser window. The temporary Bay Bank Login box will be clearly labeled. Input your current username and password and you will have access to your account and Bill Pay information. Additional information regarding Online Banking products and services will be coming over the next few weeks, so please be on the lookout for correspondences from Old Line Bank. Can I continue to use Mobile Banking and Mobile Deposit? Yes, your current mobile banking and deposit service will remain the same until June 1, Additional information regarding your mobile banking and deposit service will be coming over the next few weeks.

4 May I continue to use Remote Deposit? Yes, you will be able to continue to use your Remote Deposit as you do today. Can I still use my Bay Bank Check Card? Yes, you may continue to use your existing Bay Bank check card as normal at all Bay Bank branches and MoneyPass locations. Starting on April 14, 2018, you will also gain access to surcharge-free ATM transactions at all Old Line Bank ATM s and new access to the Allpoint ATM Network with over 55,000 surcharge-free ATM s. Do I have to change any of my direct deposits, ACH automatic debits or credit to my account? No, those items will continue to be debited or credited to and from your current account. Old Line Bank will notify the originating bank of any changes that are needed. Will I be required to get new checks? No, not at this time. You may continue to use your Bay Bank checks. You will receive Old Line Bank checks the next time you need to re-order, after June 1, Will my deposit account number change? In most cases, it will not. We understand that it is important to maintain the same account number. In the rare instance that your account number does need to change, we will supply you with new checks, a new check card and assist you in ensuring that your Online Banking, Bill Pay and any automatic debits and credits are transferred correctly. Will Bay Bank s Routing and Transit (R/T) number change? The Bay Bank R/T number will continue to be used for at least 12 months and maybe longer after the merger. As you order new checks after June 1, 2018, you will notice that the R/T number will change to the Old Line Bank R/T number. Will my loan with Bay Bank change? The terms of your loan will not change but you will notice the following changes: New Loan Number As of June 1, 2018 you will be assigned a new loan number. The new loan number will be reflected on the loan billing notices and statements that you will receive after June 1, New Payment Address As of June 1, 2018 you will see a new address to mail your loan payments. You may continue to make loan payments at any branch.

5 What new products and services will be available to me after the merger? You will notice several new products that will be available to you after the system integration on June 1, More information will follow that will highlight the new products. Will I receive additional information from Old Line Bank? Yes, over the next few weeks you will receive additional information from Old Line Bank. Our goal is to keep you informed every step of the way. You will receive another letter in late April of 2018 explaining what will happen as we merge the banking systems on June 1, You will always have full access to your account during this transition. Who do I call if I have more questions? You can call the same people you call today with any questions. The phone numbers will remain the same so feel free to contact your Bay Bank Branch or Relationship Manager. They will be available to answer any questions you may have.