How to run a tricky tray (penny social) fundraiser

⚖️ Disclaimer: Raffle laws vary by state and locality. This article is for informational purposes only and does not constitute legal advice. Before running a tricky tray raffle, check your state's permit requirements or consult a legal professional.

Most raffles are simple: buy a ticket (or multiple!) and wait for your number to be called. A tricky tray adds another layer of strategy, giving attendees dozens of prize baskets to choose from as they decide whether to spread their tickets across multiple prize buckets or go all in on one.

The best tricky tray fundraisers are built before the doors open. The prizes you source, how you structure ticket pricing, and how you keep the crowd engaged throughout the event all make the difference. This guide walks you through ten steps to running a successful tricky tray raffle, with real nonprofit examples to show you exactly what a successful raffle looks like.

Key takeaways

• Learn the lingo 🎟️ Tricky tray raffles go by many other names, including penny socials, raffle baskets, chance auctions, or brown bag auctions.
• Check your state rules 🧑‍⚖️ Raffles are regulated in most states and may require permits or have restrictions, so you'll need to check if a raffle is a viable option before you move forward.
• Create prize buckets 🪣 Instead of a single grand prize, assemble multiple buckets based on themes.
• Consider audience size 🎪 Tricky trays tend to perform best with moderate to large audiences to help create excitement and strong participation around each item drawing.
• Offer ticket bundles 💸 Increase ticket sales by offering bundled tickets, like 5 for $3 or 10 for $5.
• Use the right tools 🔧 Keep your raffle running smoothly with a platform like Givebutter, which offers free event ticketing, customizable event pages, and core fundraising and event management tools.

What is a tricky tray fundraiser?

A tricky tray raffle is a hybrid of a silent auction and a raffle. In a standard tricky tray raffle, participants buy a sheet of 25 tickets and place tickets in containers next to the prizes they want to win. Winners are drawn randomly at the end of the event.

Historically, tricky tray raffles were referred to as "Chinese auctions" or "Chinese raffles." Nonprofits today are taking a more inclusive approach by adopting alternatives like "tricky tray," "penny social," or "basket raffle."

Dive deeper

Learn the differences between a silent auction vs. a raffle →

Why is it called a tricky tray?

The name comes from the format itself: participants "trick" the system by strategically placing their tickets in the trays (containers) next to the prizes they most want to win—rather than entering a single drawing and hoping for the best.

What is a penny social?

A penny social is the same as a tricky tray raffle: participants purchase raffle tickets and decide how to distribute them across multiple baskets.

Tricky tray raffles are known by different names in different regions. Here are a few common examples: 

• Tricky tray 🎟️ Commonly heard in New Jersey and the broader Northeast
• Penny social 🎟️ A widespread name in the Mid-Atlantic 
• Basket raffle 🎟️ Common throughout the U.S. 
• Chance auction 🎟️ A more modern name
• Brown bag auction 🎟️ Less common, used in some community settings

When a tricky tray raffle works best (& when it doesn't)

Tricky tray fundraisers are ideal for events that you want to be more interactive. Instead of entering a single drawing, participants decide whether to distribute their tickets across multiple prize buckets or go all in on one prize, adding strategy and excitement to the experience.

With multiple prizes and price points, tricky tray raffles can appeal to a wide range of attendees. We’ve broken down exactly when they’re best for, and when you might want to try something else. 

When to host a tricky tray raffle 👌

• School PTAs 🏫 A wide selection of prizes works perfectly for teacher, parent, and student participants.
• Faith-based organizations ⛪ Raise money for your congregation as part of a seasonal festival or church event.
• Community-based groups 👐 Tricky tray raffles work well for large gatherings that bring local supporters together.
• Youth sports leagues ⚾ Build prize packages around sports gear or themes that appeal to both kids and parents.

When not to host a tricky tray raffle ✋

• Raffles are illegal in your state 🧑‍⚖️ Always check your state's raffle laws before you go any further.
• You only have one or two high-value prizes 💸 Tricky tray raffles require multiple prize buckets for guests to pick from.
• You expect a smaller turnout 👭 You'll need a sizeable audience to generate enough excitement across multiple raffle buckets.

How to run a tricky tray event

Whether you're hosting a tricky tray fundraiser as entertainment or as a stand-alone event, follow the steps below for an inclusive, exciting raffle.

1. Check raffle rules in your state 👩‍⚖️

Confirming that raffles are legal in your state is essential before you plan any raffle. Some states heavily restrict or prohibit raffles, while others require permits or restrict selling tickets online. Take time to research your local raffle laws and consult a legal professional if you have questions about licensing, reporting, or ticket sales.

More to explore

Get deeper insight into state raffle rules & regulations →

2. Set your fundraising goal & budget 💰

Set your fundraising goal based on a real nonprofit need (e.g., $2K to launch a new program). Then use a nonprofit event budget template to outline your anticipated expenses, such as venue, promotion, and catering. Use this formula to determine your total revenue goal:

Total expenses + fundraising goal = revenue goal

Reduce overhead costs by partnering with local venues or securing in-kind donations for food and supplies.

3. Secure your prizes 🤝

Ask local businesses, corporate sponsors, board members, or supporters to donate prizes. Craft a compelling appeal that states your fundraising goal, why it matters, and the recognition offered in exchange for raffle prizes, such as a social media shoutout or a feature in your event program.

Group donations to create themed bundles that feel cohesive and appealing to your audience. Here are some popular tricky tray prize ideas to request: 

• Experiences 🎢 Offer unique experiences like tours, classes, or local excursions to generate more excitement than standard physical prizes. 
• Food & drink 🥘 Create a chef-themed raffle basket with food and drinks or recipe books and cooking utensils. 
• Toys & games 🧸 Bundle toys, games, and family activities together to appeal to parents and kids.
• Sporting equipment 🏈 Put together sports-themed baskets with equipment, memorabilia, or tickets to local games. 
• Arts & crafts 🎨 Appeal to creative attendees with craft kits, art supplies, or specialty tools.

💡 Pro tip: Be sure to give yourself enough time to source prizes. Start at least a few months before your raffle. 

Dive deeper

Explore the ultimate list of companies that give donations for raffles →

4. Set your ticket pricing strategy 🤔

Tricky tray raffles are generally fast-paced and encourage high participation. Create pricing bundles that encourage bulk buy-ins, such as 6 tickets for $5, or 25 tickets for $20. 

Your ticket price should feel affordable while still reflecting the value of your raffle prizes. For example, if your total basket value is around $50, try a $2 ticket; if it's $120, try a $5 ticket.

💡 Pro tip: Color-code your tickets to reflect different value prize buckets. For example, yellow tickets for prizes worth $75–$100 might be $5, while red tickets for prizes worth $200–$300 might be $15. 

Dive deeper

Maximize your event ROI with our guide on how to price raffle tickets →

5. Create your prize buckets 🪣

In a tricky tray raffle, every prize or prize bundle has its own ticket bucket where participants place their entries.

Be intentional with your prize displays by using clear signage, themed decor, and visible descriptions for items or experiences that might be harder to see.

6. Promote your event 📣

The wide variety of prizes makes tricky tray raffles unique. Be sure to highlight that your event offers something for everyone.

Create a multi-channel promotion strategy that keeps your mission and the excitement of a tricky tray raffle front and center, including:

• Social media 💻 Post the details of your event and how funds raised will impact your cause. 
• Email 📧 Share information about your raffle with an email series starting at least 1–2 months in advance. 
• Word-of-mouth 💬 Spread the word in your community and ask your board members to do the same. Consider assigning each board member a ticket quota. 
• Print marketing ✉️ Don’t underestimate the power of direct mail. Send flyers to your supporters and hang them up in your community. 

💡 Pro tip: Tricky tray events add a gamified element that not all raffle activities have. Highlight that appeal in your promotions to create friendly competition and boost engagement.

7. Sell tickets 🎫

Launch ticket sales a month in advance and consider offering early-bird incentives. Assemble a team of volunteers to sell tickets, answer questions, and keep lines moving efficiently on event day. Some nonprofits include a set number of tickets with entry and sell additional ticket bundles separately.

Simplify ticket sales with a platform like Givebutter, which lets you create customized event ticketing pages, process payments, and track event data in one place.

8. Run a smooth event 🎊

A smooth tricky tray raffle starts with outlining the rules to ensure everyone is on the same page. Be clear about how long guests will have to browse prizes and when ticket sales will end. When it's time, pull a winning number from each bucket or use Givebutter's random number generator.

9. Complete IRS reporting 📊

Raffle events may trigger specific IRS reporting requirements depending on the prize value. If the prize is over $600 and is at least 300x the ticket price, nonprofits may need to issue Form W-2G to the winner.

Federal income tax withholding may apply to prizes over $5K. Always consult a tax professional to ensure your raffle complies with current IRS regulations.

10. Get feedback & steward participants 🪼

Your event isn't over once the last prize is claimed. In fact, it's an essential time to cultivate new donor relationships. Plan your post-event touchpoints before your event so your follow-up efforts stay consistent and intentional.

Your post-raffle donor stewardship plan might look something like this: 

• Immediate thank you 💛 Within 48 hours, send a message to each participant and donor expressing your appreciation. 
• Feedback survey 🗳️ Send your attendees a brief survey to gauge how your event went and improve next time. 
• Impact reporting 📈 Within 2–3 weeks, share how the money fundraised during your raffle has helped advance your mission. 
• Opportunities for deeper involvement 🙌 Offer supporters more ways to get involved, like signing up for your newsletter, volunteering, or attending future events.

More to explore

Get up to speed on the best raffle sites for an unforgettable nonprofit raffle →

Real tricky tray fundraiser examples

1. ECF Growing Hope Tricky Tray 🌱

The ECF Growing Hope Tricky Tray raised $7K+ from 92 supporters for Emmanuel Cancer Foundation. The event structure: $30 admission included a tier 1 ticket sheet and a door prize entry, with 4 prize tiers plus a golden ticket.

⭐ Best for: PTAs, large community events, faith-based organizations.

💛 Make it your own: Bundle a ticket sheet into your admission price so every attendee walks in already entered, then offer additional ticket bundles on site to drive revenue throughout the event.

2. Bloomin' Baskets Tricky Tray 🮺

Bloomin' Baskets raised $3K+ from 98 supporters for Adath Shalom, already reaching 98% of its $5K goal weeks before the event. With 200+ prizes and baskets across three tiers, ticket sheets starting at $10, and a 50/50 raffle running alongside the main event, the event gives attendees plenty of ways to participate.

⭐ Best for: Faith-based organizations, community events, schools.

💛 Make it your own: Use tiered prize buckets to appeal to a wider range of attendees and share the value range of each tier directly on your event page so supporters know exactly what they're playing for before they arrive.

Plan your next tricky tray raffle with Givebutter

Running a great tricky tray takes real coordination, but with the right plan in place, you have everything you need to pull off an event your community will love. Use this guide as your planning checklist and revisit it each year to tighten up what worked and fix what didn't.

Givebutter handles the fundraising side so you can focus on the experience. Sell tickets online, build a customizable event page to drive pre-event buzz, and track attendee and ticket data in one place so you can report results back to your team and make smarter decisions for next year, all for free.

Sign up for Givebutter and start planning your next tricky tray fundraiser.

FAQs about tricky tray events

Can you run a virtual tricky tray raffle?

You may be able to—and many nonprofits do. The most common approach is a hybrid: sell tickets online, let supporters choose which baskets they want to enter, then have volunteers drop those entries into physical buckets before a live or livestreamed drawing.

A platform like Givebutter makes it easy to set up an event page, list each basket as its own virtual bucket, sell ticket bundles, and share results with participants. Just make sure online raffle ticket sales are permitted where your organization and participants are located before you launch, and consult a legal professional if you're unsure.

How many prizes should a tricky tray have?

Smaller tricky tray raffles should have at least 10 to 30 prizes. A general rule of thumb is to prioritize variety and quality of prizes over quantity, while ensuring that each of your raffle participants has a reasonable chance of winning.

How do you price tricky tray tickets?

Price your tricky tray tickets based on the value of your prizes. Higher-value items typically support higher ticket prices, while lower-value baskets should remain more affordable.

Offer ticket bundles, like 1 sheet for $10, 3 sheets for $25, and 5 sheets for $35, to encourage larger purchases.

How long should a tricky tray event last?

If you're hosting a standalone tricky tray raffle, aim for 2–3 hours. You'll need enough time for guests to browse all the prize buckets, purchase tickets, and place their entries before the drawing begins.