Your 2024 Vendor Cheat Sheet: 25 Booths You Absolutely Cannot Miss at This Year's Chestertown HP Fest

Let's be honest: the Chestertown Homecoming Festival is big enough that showing up without a plan means you'll spend half your time wandering and the other half realizing you missed the thing you actually wanted. We've done the legwork so you don't have to.

Below is your complete insider guide to 25 vendors worth going out of your way for this year. We've organized them by category, flagged the ones that sell out fast, and included a few tips straight from the vendors themselves. Print this out, screenshot it, or just read it twice before you leave the house. Either way — you're welcome.

Pro tip before we dive in: Arrive early. Seriously. The first hour after gates open is when the crowds are thinnest and the best inventory is fully stocked. For food vendors specifically, the lunch rush (roughly 11:30am–1:30pm) can mean long waits. Plan your eating around it.

Food and Drink: The Essentials

1. The Kettle & The Cauldron This is the booth that started the whole butterbeer cupcake legend, and it continues to deliver. Owner and baker Marlene has been a fixture at the festival for years, and her cream cheese frosting game is genuinely unmatched. She now offers a full lineup of wizarding-inspired sweets alongside her classic Maryland treats. Get there within the first 90 minutes or prepare to be disappointed. Insider tip: Ask about the "secret menu" seasonal item — she always has one and it's always worth it.

2. Bay Side BBQ Co. Slow-smoked brisket, pulled pork, and the best baked beans you're going to find anywhere near the Eastern Shore. The line looks intimidating but moves faster than you'd think. Their brisket sandwich with house-made pickles is the move. Arrive by 11am to beat the lunch crowd.

3. Chester River Creamery Local dairy, small-batch flavors, and genuinely creative seasonal offerings. This year they're debuting a blackberry lavender soft serve that has been described by early testers as "unreasonably good." Cash or card accepted.

4. Spice & Tide Seasonings Not exactly food, but absolutely food-adjacent. This local spice vendor brings hand-blended seasoning mixes that make excellent gifts and even better additions to your home cooking. Their Old Bay-adjacent "Shore Blend" is a perennial bestseller.

5. The Pretzel Barn Hand-twisted, fresh-baked soft pretzels with an array of dipping sauces that goes well beyond the standard mustard situation. The cinnamon sugar version with cream cheese dip is a festival tradition for a reason.

6. Honeybee Hill Apiary Local raw honey in a dozen varieties, plus beeswax candles and lip balms. The vendor — a third-generation beekeeper from just outside Chestertown — is genuinely one of the most knowledgeable people you'll talk to all day. Ask her about the wildflower varietal.

7. Chesapeake Cold Brew If you need caffeine and you need it to be good, this is your stop. Small-batch cold brew coffee sourced from a Maryland roaster, served in reusable cups (bring yours back for a discount). They also do a brown sugar oat milk version that's been known to convert dedicated hot coffee people.

Artisan Goods and Handmade Crafts

8. Wand & Wick Candle Co. Possibly the most Instagram-friendly booth at the entire festival. Hand-poured soy candles with names drawn from fantasy literature and local geography. Their "Chesapeake Midnight" and "Enchanted Orchard" scents are festival exclusives you won't find in their regular online shop. Limited quantities — don't sleep on this one.

9. Ironwood Leather Goods Custom-tooled leather wallets, journal covers, and key fobs, many featuring house crest and fantasy-inspired designs. The craftsman does live demonstrations throughout the day, which is worth watching even if you're not buying.

10. Tidewater Watercolors Local artist Sarah Vance reimagines Chestertown's historic architecture through a whimsical, slightly fantastical lens. Her prints make genuinely excellent souvenirs and she offers custom commissions for pickup at the festival's end. Ask about the festival-exclusive print — she creates a new one each year.

11. Moonstone & Moss Jewelry Handcrafted sterling silver and gemstone jewelry with a nature-meets-mythology aesthetic. The earring selection alone is worth the stop. Prices range from very accessible to "treat yourself" territory.

12. The Bookbinder's Bench Handmade journals, notebooks, and sketchbooks in leather and fabric covers. If you're a stationery person, budget extra time here because you will not leave quickly.

13. Eastern Shore Woodcraft Turned wooden bowls, cutting boards, and small décor items made from locally sourced Maryland hardwoods. Everything is one-of-a-kind by definition. The vendor, a retired teacher who took up woodworking ten years ago, will happily tell you which tree each piece came from.

14. Bramble & Bloom Floral Dried flower arrangements, wreaths, and botanical prints sourced from the vendor's own farm. The fall harvest arrangements are timed perfectly for the festival season and make immediate sense as home décor.

Apparel, Accessories, and Wearables

15. House Colors Knitwear Hand-knitted scarves, hats, and fingerless gloves in an array of color combinations that will absolutely speak to a certain type of festival attendee. The vendor takes custom orders for pickup at the festival — contact her through the festival website ahead of time.

16. Shore Style Apparel Local graphic tees and sweatshirts celebrating Chestertown and the broader Eastern Shore. Their annual festival-exclusive design always sells out, and this year's version reportedly features a design that bridges local landmark imagery with a subtle nod to the HP community. Very wearable.

17. The Patched Path Iron-on and sew-on patches in a huge variety of designs, plus custom embroidery services. Great for personalizing bags, jackets, and hats on the spot.

18. Fox & Fern Vintage Carefully curated vintage clothing and accessories with a focus on wearable, practical pieces. The vendor has a particular gift for sourcing items that look like they could have come from a wizarding wardrobe without being costume-y about it.

Specialty, Wellness, and Unique Finds

19. Chesapeake Herbals Dried herb bundles, tinctures, herbal teas, and botanical skincare made from locally grown plants. The vendor is a certified herbalist and genuinely happy to chat through what might work for you. Their "Evening Calm" tea blend is a bestseller for good reason.

20. The Potion Shelf Okay, it's not actually potions — but this bath and body vendor leans fully into the wizarding aesthetic with beautifully labeled bath salts, sugar scrubs, and shower steamers. The packaging alone makes these perfect gifts. Festival discount: mention the HP Fest website for 10% off.

21. Stargazer Ceramics Hand-thrown pottery including mugs, bowls, and small decorative pieces. The vendor fires everything herself in a wood kiln, which gives each piece a distinctive warmth. Mugs are the most popular item and go fast.

22. Maryland Made Marketplace A collective booth featuring goods from several small Maryland producers — hot sauces, jams, pickles, and specialty pantry items. Think of it as a curated Eastern Shore grocery store in booth form. Great for gifts.

23. The Curious Bookshelf Used and rare books with a particular focus on fantasy, folklore, and Maryland local history. The vendor has a gift for curation and always shows up with at least a few genuinely surprising finds. Cash preferred.

24. Wandering Wicks & Wonders A catch-all booth of whimsical small goods — enamel pins, stickers, mini prints, and assorted curiosities. Budget-friendly and great for kids. The enamel pin selection has a strong HP-adjacent section this year.

25. Riverside Community Market The festival's community booth, run by local organizations and nonprofits. Stop here to learn about what's happening in Chestertown year-round, pick up information about upcoming events, and grab a few locally made goods with proceeds going back into the community.

A Few Final Tips Before You Go

• Bring cash. Most vendors accept cards, but a few smaller artisans prefer cash and some offer cash discounts.
• Wear comfortable shoes. The festival grounds are larger than they look on the map.
• Check the HP Fest website the morning of for any last-minute schedule or location changes.
• Come hungry and come curious. The best discoveries at any festival are the ones you didn't plan for.

See you out there, Chestertown.