Trolley Tour Details

Live Baltimore is committed to making our events accessible to everyone. If you require an accommodation or service to fully participate in Trolley Tour, please get in touch with our Events Manager at events@livebaltimore.com at least two weeks prior to the event. In all situations, a good-faith effort will be made to provide reasonable accommodations.

Please note that there are limited designated accessible parking spots in the parking area, marked on the ground. These limited spots are on a first-come, first-served basis.

There are two paid garages within walking distance of the Trolley Tour location. Please note that the parking surrounding the school is limited to 1-hour parking only.

• Lot 1: Lexington Street Garage located at 660 W Lexington St — paid parking garage at a rate of $17 per car.
• Lot 2: Poppleton Street Garage located at 1 N Poppleton St — paid parking garage at a rate of $10 per car.
• Park elsewhere at your own risk and expense. Live Baltimore is not responsible for any parking fees, tickets, or towing charges you might incur.

View the map below for garage locations.

• There are 4 on-site accessible spots for attendees on a first-come, first-served basis. Note the location circled in red on the map below.
• You MUST either display your accessible hang tag or have a registered license plate. The school’s security will be patrolling the lot and they will tow.
• Attendees may also be dropped off by the entrance doors (marked by the red star on the map).
• PLEASE DO NOT PARK IN THE ACCESSIBLE SPOTS MARKED FOR VENDORS.

Children are welcome at the event and must always be accompanied by a parent or guardian. There are no child-specific activities or childcare available at Trolley Tour. 

Your schedule includes two workshops of your choosing. Each time slot presents five options; select one for each. Below, you’ll find information on workshops in the same time slot, along with descriptions to help you decide which ones are best for you!

Time Slot #1

Ask a Lender: Experts suggest meeting three lenders before choosing one for your home loan. Knock out those interviews in this workshop featuring three pros ready to answer your burning mortgage questions.

Single & Searching for a Home: Join this workshop to discover tips and tricks for affording a home and navigating the homebuying process as a single homebuyer.

Habitat Chesapeake First-Time Affordable Homebuying Program: Are you making enough to pay a monthly mortgage but not enough to qualify for traditional bank loans? Learn more about the Habitat for Humanity of the Chesapeake Homeownership Program, which offers a 0% interest loan to eligible buyers.

10 Keys for Successful Homebuying: Get the tools and information you need to feel empowered to make informed decisions when buying a home.

How to Purchase a City-Owned Property: Join us for a brief overview of purchasing a vacant property from Baltimore City’s Department of Housing and Community Development.

Time Slot #2

Down Payment Assistance 101: This panel discussion will review the details and qualifications for various Baltimore City and Maryland Mortgage Program down payment and closing cost incentives.

What to Expect at Closing: This workshop helps first-time homebuyers understand title, why it matters, and how to prepare for closing day, so you know exactly what to expect when it’s time to get the keys.

Purchase & Improvement Loan Program: The Healthy Neighborhoods Program provides low-interest purchase & rehab, refinance & rehab, and home improvement loans in over 40 Baltimore communities.

6 Things First-Time Buyers Need to Know: Whether you’re new to homebuying in general or just new to buying in Baltimore City, we’ll walk you through six critical items you‘ll need to understand to make that big purchase a little easier.

Getting a Home Inspection and Negotiating Repairs: This workshop will cover what to expect from a home inspection, a buyer’s options after the inspection, and the next steps.

The Spring 2026 Trolley Tour will explore Southwest Baltimore City.

There will not be any stops along the tour. While we won’t be going into homes, our tours are always focused on residential neighborhoods, where many examples of homes will be on display. The tour includes neighborhood home price information and other metrics such as walk, transit, and bike scores. Live Baltimore also provides a list of open houses available the same day as the event and encourages participants to continue their day by visiting them.

Just to let you know, the $5,000 Buying Into Baltimore incentive can be used citywide. It does not need to be used in a neighborhood that we tour.

Neighborhoods we will be touring include:

• Barre Circle
• Downtown
• Federal Hill
• Franklin Square
• Heritage Crossing
• Hollins Market
• Inner Harbor
• Mount Vernon
• Poppleton
• Ridgely’s Delight
• Seton Hill
• Sharp-Leadenhall
• Union Square
• Upton
• Washington Village/Pigtown

No. Homebuyers who have not yet received their homeownership counseling certificate are welcome to attend Trolley Tour events.

However, please be aware that you must earn a homeownership counseling certificate from a City-approved agency in order to be eligible for the related $5,000 incentive. Because the number of these awards is limited for each event, Live Baltimore recommends that you complete counseling prior to the event date if you intend to apply for the incentive.

The $5,000 Buying Into Baltimore Incentive is the only downpayment incentive that requires Trolley Tour attendance to qualify to apply. Click here to view a video explaining the incentive process.

To participate in the incentive lottery, applicants must:  

• Earn a counseling certificate from a City-approved agency before making an offer on a home.  
• Attend the Trolley Tour event before making an offer on a home.  
• After the event, make an offer on a home and secure a contract within 12 business days. 

Twenty Buying Into Baltimore incentives are awarded by lottery AFTER each Trolley Tour event. To learn more and apply, visit LiveBaltimore.com/lottery and follow the steps to submit your application.  

Incentive money is distributed at settlement. Please note that your chances of receiving the incentive depend on the number of eligible applicants and vary by event. Also note that one contract equals one entry, meaning two people buying a home together will not be entered into the lottery twice.

To increase chances of receiving an award, Live Baltimore recommends that homebuyers complete homeownership counseling, obtain a mortgage loan pre-qualification, and meet with a real estate agent prior to attending Trolley Tour. 

View the video below for full details of the $5,0000 Buying into Baltimore incentive.

$5,000 Incentive Timeline for Spring 2026 Trolley Tour:

• May 9: Trolley Tour Event
• Before placing an offer on a home, earn your Homeownership Counseling Certificate from a City-approved counseling agency
• Between May 9 and May 27 by 2 pm: Secure a contract on a home
• May 11: Lottery application portal opens
• May 27 by 2 pm: Applications are due; Verification appointment must be completed
• May 29 at 12 pm: Lottery held at facebook.com/livebaltimore
• Must close by: August 27, 2026

If you have any questions or issues during this process, please email lottery@livebaltimore.com or call (410) 637-3750 ext. 118. You can find additional homebuying information and resources here.

$5,000 Incentive Timeline for Spring 2026 Trolley Tour:

• May 9: Trolley Tour Event
• Before placing an offer on a home, earn your Homeownership Counseling Certificate from a City-approved counseling agency
• Between May 9 and May 27 by 2 pm: Secure a contract on a home
• May 11: Lottery application portal opens
• May 27 by 2 pm: Applications are due; Verification appointment must be completed
• May 29 at 12 pm: Lottery held at facebook.com/livebaltimore
• Must close by: August 27, 2026

If you already have an offer on a home, you can still enjoy Trolley Tour. There will be workshops geared towards people very far along in the homebuying process.

Please note that if you already have an offer on a home, you cannot qualify to apply for the $5,000 incentive lottery. To be eligible to apply, your offer must be dated on or after May 9, 2026, the date of the Trolley Tour, and no later than May 27, 2026.

To be eligible to apply, your offer must be dated on or after May 9, 2026, the date of the Trolley Tour, and no later than May 27, 2026, by 2 pm.

You may not enter into a contract of sale on the home you wish to purchase using the $5,000 incentive until the day of the Trolley Tour event. This means, do not make an offer on your target property until after you have attended the Trolley Tour event. There is a 12-business-day time frame from the day of the event in which homebuyers must secure a ratified contract of sale on qualifying properties. A limited number of homebuyers who successfully complete and submit their incentive paperwork will be drawn from a pool of eligible applicants and subsequently receive the incentive.

$5,000 Incentive Timeline for Spring 2026 Trolley Tour:

• May 9: Trolley Tour Event
• Before placing an offer on a home, earn your Homeownership Counseling Certificate from a City-approved counseling agency
• Between May 9 and May 27 by 2 pm: Secure a contract on a home
• May 11: Lottery application portal opens
• May 27 by 2 pm: Applications are due; Verification appointment must be completed
• May 29 at 12 pm: Lottery held at facebook.com/livebaltimore
• Must close by: August 27, 2026

Visit LiveBaltimore.com/lottery for the full details and steps on how to apply for the incentive.

View the video below for full details of the $5,0000 Buying into Baltimore incentive.

Incentive money is distributed at settlement, not at Trolley Tour.

Live Baltimore is not responsible for the distribution of incentive funds. Incentive funds are provided and regulated by Baltimore City’s Department of Housing and Community Development.

Please note that your chances of receiving the incentive depend on the number of eligible applicants and vary by event. Also note that one contract equals one entry; meaning two people buying a home together will not be entered into the lottery twice.

Read more about the incentive here or contact the Baltimore City Department of Housing and Community Development’s Office of Homeownership at (410) 396-1319.