Winter is the most generous season of the year. Between Thanksgiving and the New Year, charitable giving spikes dramatically, and people are primed to participate in fundraisers. Whether you are planning a holiday gala reverse raffle, a Christmas bazaar basket raffle, or a winter community fundraiser, the right prizes make all the difference. Here are 25+ winter-themed raffle ideas organized by category, with sourcing tips and a month-by-month timing guide for the November-February season.
Holiday Gift Baskets
Holiday-themed baskets are the bread and butter of winter raffle fundraisers. They photograph beautifully for promotion, they are easy to assemble from donated items, and they tap into the gift-giving mood of the season.
1. Christmas Baking Bonanza
Fill a large mixing bowl with holiday cookie cutters, premium vanilla extract, sprinkles, a rolling pin, an apron, cookie mixes, and a recipe book. Add a $25 gift card to a kitchen supply store. This basket appeals to bakers and parents alike. Estimated value: $60-$100. For more ideas like this, explore our complete raffle basket ideas guide.
2. Holiday Movie Night Package
A streaming service gift card, a cozy fleece blanket, microwave popcorn, hot cocoa mix, candy canes, and a set of classic holiday movie DVDs or a curated movie list card. Package it all in a holiday-themed basket or popcorn bucket. Estimated value: $50-$85.
3. Gourmet Holiday Food Basket
Premium cheeses, artisanal crackers, fine chocolates, a bottle of wine or champagne, specialty jams, nuts, and dried fruits. Present it in an elegant basket with a ribbon. Local specialty food shops often donate items for these baskets in exchange for event recognition. Estimated value: $75-$150.
4. Holiday Entertaining Bundle
A set of wine glasses, a cheese board, cloth napkins, candles, a bottle of wine, and a holiday tablecloth or table runner. Perfect for the person who loves hosting holiday gatherings. Estimated value: $80-$125.
Cozy Night In Bundles
Winter makes people crave warmth and comfort. These baskets sell themselves.
5. Ultimate Cozy Night Bundle
A plush throw blanket, fuzzy socks, scented candles, a best-selling novel, herbal tea assortment, and chocolate truffles. This is one of the most reliable sellers at any winter raffle because nearly everyone wants it. Estimated value: $60-$100.
6. Hot Chocolate Lovers Collection
Gourmet hot cocoa mix from 3-4 different brands, a set of oversized mugs, marshmallows, peppermint sticks, whipped cream canister, and a electric milk frother. Simple to assemble, high visual appeal. Estimated value: $40-$70.
7. Coffee Connoisseur Basket
Whole bean coffee from local roasters, a French press or pour-over set, a coffee grinder, biscotti, and a gift card to a local coffee shop. Coffee lovers will compete for this one. Estimated value: $60-$100.
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Ski and Winter Sports Packages
For communities near ski areas or in cold-weather regions, winter sports prizes are natural crowd-pleasers.
8. Ski Day Package
Lift tickets for two at a local ski resort, plus a gift card for equipment rental. Add hand warmers, a neck gaiter, and a thermos. Partner with the resort for donated or discounted tickets. Estimated value: $150-$400.
9. Snowboard Starter Kit
A snowboard (check local sporting goods stores for end-of-season clearance or donations), boots, bindings, and a lesson voucher. This works as a premium grand prize. Estimated value: $300-$600.
10. Ice Skating Experience
Tickets to a local ice rink, skating rental vouchers, hot cocoa, and a gift card to a nearby restaurant. Low cost to assemble, strong family appeal. Estimated value: $50-$80.
11. Winter Sports Gear Bundle
A sled or toboggan, insulated water bottles, hand and toe warmers, a winter hat and glove set, and a $25 gift card to a sporting goods store. Great for families with kids. Estimated value: $75-$125.
New Year's Eve and Celebration Prizes
12. New Year's Eve Party Kit
A bottle of champagne or sparkling cider, champagne flutes, party hats, noisemakers, confetti poppers, and a $50 restaurant gift card for New Year's dinner. Festive and fun. Estimated value: $75-$125.
13. Countdown to Midnight Basket
A fancy clock or watch, party supplies, appetizer ingredients or gift cards, a playlist card with QR code to a curated Spotify playlist, and sparklers (where legal). Estimated value: $60-$100.
14. Resolution Kickstart Package
A fitness tracker, yoga mat, water bottle, healthy cookbook, and a month membership to a local gym or fitness studio. January timing makes this particularly relevant. Estimated value: $100-$200.
Winter Getaway Experiences
Experience prizes drive the strongest ticket sales at winter fundraisers because they offer an escape from the cold-weather routine. For more high-value prize inspiration, see our complete raffle prize ideas guide.
15. Winter Cabin Getaway
A two-night stay at a cabin or lodge, paired with a restaurant gift card and firewood delivery. Partner with local vacation rental owners or lodges for donated stays. Estimated value: $300-$700.
16. Spa Day Retreat
A massage and facial package at a local spa, plus a plush robe, bath bombs, and candles. Winter is the perfect time to market this as a "warm escape from the cold." Estimated value: $150-$300.
17. Dinner and a Show
Tickets to a local theater production, ballet (The Nutcracker in December), or comedy show, paired with a dinner gift card at a nearby restaurant. Estimated value: $100-$250.
18. Wine Country Weekend
A tasting room pass for two at a local winery or wine trail, paired with a wine carrier, cheese board, and crackers. Many wineries offer discounted tasting packages for charitable events. Estimated value: $100-$200.
Kids and Family Winter Fun
19. Snow Day Survival Kit
Board games, puzzles, card games, popcorn, hot cocoa packets, coloring books, and craft supplies. Parents will fight for this basket when school is cancelled. Estimated value: $50-$80.
20. Build-Your-Own Gingerbread House
A gingerbread house kit (or two), extra candy decorations, icing, and a family photo frame for the finished masterpiece. Affordable to assemble and very photogenic. Estimated value: $25-$45.
21. Winter Reading Bundle
Age-appropriate books (ask a local bookstore for recommendations), a reading light, bookmark set, a cozy blanket, and a library gift card. Promote literacy while giving a great prize. Estimated value: $50-$75.
High-Value Grand Prizes for Reverse Raffles
Winter reverse raffle dinners are hugely popular. The holiday spirit plus an evening out makes for excellent attendance. These grand prizes justify premium ticket prices and create the excitement that makes reverse raffles unforgettable. Check our holiday fundraising raffles guide for a deep dive into running holiday events.
22. Cash Grand Prize
A $5,000 or $10,000 cash prize is the most reliable ticket seller for reverse raffle events. With 200-500 tickets at $50-$100 each, the math works beautifully for fundraising margins. Cash prizes are particularly appealing during the holiday season when people have extra expenses.
23. Tropical Vacation Escape
A travel agency voucher for $2,000-$5,000 toward a warm-weather getaway. Position this as "escape the winter" and it practically sells itself. Partner with a travel agency for potentially donated or discounted packages. Estimated value: $2,000-$5,000.
24. Home Electronics Package
A large-screen TV, soundbar, and streaming device. Winter is when families settle in for movie nights and sports watching. Always a strong seller. Estimated value: $500-$1,500.
25. Holiday Shopping Spree
A collection of gift cards totaling $500-$1,000 from popular retailers (Amazon, Target, local shops). This has universal appeal because winners choose their own gifts. Easy to source by asking local businesses to each contribute a gift card. Estimated value: $500-$1,000.
26. Luxury Watch or Jewelry
Partner with a local jeweler for a donated or discounted piece. Watches and jewelry are classic winter raffle prizes that photograph well and drive ticket sales. Estimated value: $300-$1,000.
Winter Raffle Timing Calendar
November: Pre-Holiday and Thanksgiving
- Thanksgiving-themed events (gratitude dinners, community feasts)
- Early holiday shopping basket themes
- Fall-to-winter transition events
- Giving Tuesday tie-ins (first Tuesday after Thanksgiving)
December: Peak Holiday Season
- Christmas parties and galas (first two weeks of December are ideal)
- Holiday bazaars and craft fairs with basket raffles
- Church Christmas dinner reverse raffles
- Avoid December 15-31 when personal holiday commitments peak
January: New Year and Fresh Starts
- New Year resolution-themed prizes (fitness, wellness, learning)
- Winter sports season is in full swing
- Post-holiday "treat yourself" themed baskets
- Martin Luther King Jr. Day weekend events
February: Valentine's and Winter Wrap-Up
- Valentine's Day dinner raffles with romantic prize themes
- Couples' experience prizes (dinner, wine tasting, spa day for two)
- Super Bowl party raffle events
- Presidents' Day weekend events
For the season that follows, our spring raffle ideas guide picks up right where winter ends. And for fall events leading into winter, see our fall fundraiser raffle ideas.
Tips for Winter Raffle Success
Leverage Holiday Generosity
People are more generous in November and December than any other time of year. Use this to your advantage when approaching businesses for prize donations and when marketing ticket sales. Frame your raffle as a way to give back during the holiday season.
Create Instagram-Worthy Displays
Winter baskets lend themselves to beautiful presentation. Use holiday-themed wrapping, ribbons, and props. Take photos and share them on social media in the weeks leading up to the event to build anticipation and drive early ticket sales.
Pair with a Reverse Raffle for Maximum Revenue
Winter dinner events are perfect for reverse raffles because people are already looking for evenings out during the holiday season. The format keeps everyone at the table all night, which means more bar and concession revenue on top of ticket sales. Get started with rafflr today to run your winter reverse raffle with professional software.
Start Collecting Prizes Early
Begin soliciting prize donations in September or October, before businesses are overwhelmed with holiday donation requests. The earlier you ask, the more likely you are to get quality prizes and the more time you have to curate impressive baskets.
Offer Multi-Ticket Pricing
For basket raffles, offer deals like "1 ticket for $5, 3 for $10, arm's length for $20." For reverse raffle events, consider early-bird pricing or group discounts (buy a table of 8 tickets and get a discount). These bundles increase average spend per attendee.
Bottom Line
Winter fundraisers benefit from the natural generosity of the holiday season, the desire for social gatherings during cold months, and the universal appeal of holiday-themed prizes. By curating prizes that match the season and running your event with a format that maximizes engagement, your winter raffle can be the fundraising highlight of the year.
Mix your prize tiers: high-value grand prizes for reverse raffle events, mid-range experience prizes that people dream about, and affordable baskets that are inexpensive to assemble but irresistible to bid on. Plan early, promote creatively, and deliver an event experience that has people asking "when is next year's raffle?" before they leave the building.