Fall in Fairfield County is pure magic. Crisp air, golden foliage, and weekend plans that practically write themselves. If you’re looking to make the most of the season, here’s a complete Fairfield County Fall Bucket List filled with local farms, festivals, and hidden gems.
1. Pick-Your-Own Apples 🍎
- Silverman’s Farm (Easton) – Known for its orchards and farm store.
- Beardsley Cider Mill (Shelton) – Famous for fresh-pressed cider and cider donuts.
Nothing says fall like warm donuts and a bag full of apples.
2. Pumpkin Patch Adventures 🎃
- Jones Family Farms (Shelton)
- Blue Jay Orchards (Bethel)
Whether you’re carving or just decorating your front porch, these farms deliver the perfect pumpkins.
3. Can’t-Miss Fall Festivals 🍂
- Trumbull Arts Festival (Sep 14)
- Stratford Apple Festival (Sep 20)
- Puttin' On The Dog, Greenwich (Sep 21)
- Waveny Arts Festival, New Canaan (Sep 28)
- Newtown Arts Festival (Sep 26-28)
- The NICE Festival, Norwalk (Oct 4)
- Earthplace Fall Festival, Westport (Oct 5)
- New Canaan Nature Center Fall Fair (Oct 10–12)
- That's Amore Italian Festival, Stamford (Oct 11-12)
Think live music, local vendors, and fried fair food.
4. Corn Maze Fun 🌽
- Plasko’s Farm (Trumbull)
- Castle Hill Farm (Newtown)
Perfect for families — or testing your navigation skills at night.
5. Haunted Fun 👻
- Blood Manor (Stamford)
- Phantom Fall Fest at Lake Compounce (worth the drive!)
- Harvest Fair After Dark (Fairfield)
Because no fall bucket list is complete without a little scare.
6. Brews & Ciders at Oktoberfest🍻
- Fairfield Oktoberfest (Sep 13)
- Spacecat Oktoberfest, Norwalk (Sep 20)
- 314 Oktoberfest, Norwalk (Sep 28)
- Darien Oktoberfest (Oct 4)
Pumpkin beer, hard cider, and cozy tasting rooms = peak autumn.
7. Leaf-Peeping Hikes 🍁
- Devil’s Den Preserve (Weston)
- Trout Brook Valley (Easton)
- Bartlett Arboretum (Stamford)
- Lake Mohegan (Fairfield)
Pack a sweater and catch the golden-hour glow.
Final Thoughts
Fairfield County offers endless ways to celebrate the season — whether you’re sipping cider, exploring corn mazes, or catching peak foliage on a local trail. This fall bucket list is just a starting point to soak up everything autumn has to offer.
As someone who lives and works right here in Fairfield County, I don’t just keep tabs on local homes — I keep tabs on what makes this community such a special place to call home. If you’re considering a move (or just curious what your home might be worth in today’s market), let’s connect. I’d love to share both my local insight and how I can help you make your next move seamlessly.
Contact me to get started:
📞 Joe Balestriere, Realtor®
📲 Call/Text: 203-216-0670
