This family-friendly event will feature cookout-style food as well as items for sale. Not restricted to boats and boating equipment/services. Vendors can showcase locally made crafts, unique jewelry, one-of-a-kind gifts, clothing, tools, and much more! Vendor reservations are only $25 for a 9x18-foot space. Additionally, members of the Hartford Power Squadron will be available to help boaters access information on our courses, including the basic water safety class that qualifies students to obtain their required certification from the state of Connecticut.

💰 $25⭐ Juried🌳 Outdoor

📅 Feb 28, 2026

Chili Fest

📍 Old Saybrook, CT• Main Street

The 29th Annual Chili fest takes place along Main Street, Old Saybrook. Over 25 chefs will compete for the title of "Best Chili,". Tasting ballots are sold at the Chamber office (1 Main Street) and at ballot stations along Main Street. Each ballot allows purchaser to sample all chilis. Mark your ballot with your top choice and return to a ballot station. 10 chilis must be tasted for your vote to count. Proceeds support the Chamber's C. Wilfred Hunter Memorial Scholarship for graduating high school seniors attending post-secondary school. In addition, the top three winners earn a donation to their designated charity.

💰 $50⭐ Juried🏠 Indoor🌳 Outdoor

📅 Nov 15, 2025🔁 Recurring

Saint Paul Christmas Fair

📍 Old Saybrook, CT• St. Paul Lutheran Church

This Connecticut Holiday Celebration will have antique/collectibles, commercial/retail, crafts, fine art, fine craft and flea market exhibitors, and 1 food booth. This event will also include: white elephant, basket silent auction, raffle as well as lunch.

🏠 Indoor🌳 Outdoor

🔗 Quick Links

🛒Booth Essentials

⛺10x10 Canopy + SidewallsVendor pick 🪑6ft Folding TableVendor pick 🎨Stretch Table CoverVendor pick ⚖️Tent WeightsFrom $30 🌀Hanging Tent FanVendor pick 📋Sign HoldersFrom $25

Full vendor supply list →

Tents, tables, displays, card readers, packaging and signage.

🧪 Make What You Sell?

If you make soap, candles, wax melts, or bath & body products, our sister site Soaply has free calculators for exact recipes, lye, and pricing.

Try Soaply's free maker calculators ↗

📍 Other Cities in Connecticut

Manchester(7)Hartford(6)Fairfield(5)Middletown(5)Southbury(5)South Windsor(5)Danbury(4)New Haven(4)Milford(4)Cromwell(3)

Vending in Old Saybrook?

Pro members get distance-based search, expense tracking, and deadline alerts.

Try Pro Free →

Never miss an Old Saybrook, CT craft fair

We add new Old Saybrook, CT events every week. Get a free email heads-up when fresh fairs and application deadlines go live, whether you are going to shop or sell.

No spam. Unsubscribe anytime.

Selling at Old Saybrook, CT fairs?

Pro turns the directory into a way to run your booth business:

✓Track booth profit and ROI for every fair you work
✓Log expenses and sales to see which shows are worth it
✓Deadline reminders so you never miss an application
✓See new Old Saybrook, CT fairs 7 days early

Start a free 14-day trial →

No credit card required. $15/mo or $120/yr after.

About Craft Fairs in Old Saybrook, Connecticut

Old Saybrook hosts 4 craft fairs, art shows, and artisan markets throughout the year. Whether you're a local vendor or traveling to sell your handmade goods, TheCraftMap helps you find the best events in Old Saybrook with booth fee details, application deadlines, and vendor reviews.

Looking for more events? Browse all craft fairs in Connecticut or use our calendar view to plan your 2026 craft fair season. Our ROI calculator can help you estimate whether a fair is worth the trip.