NEXT FIRST FRIDAY OCTOBER 2..✨✨ 🎉  🎉✨

First Fridays in Middlebury are presented by Better Middlebury Partnership with the generous support of the National Bank of Middlebury.

October’s First Friday is shaping up to be a goodie!  Downtown shops, restaurants, galleries, and businesses will be joining in, creating one of those classic Middlebury fall evenings where music spills into the streets, friends bump into one another, and there’s something happening around every corner.

Wander downtown and pop into:

*Shiretown- Pop Up dinner…OKTOBERFEST!!  reservations required! See Shiretown website and socials for details!

Town Hall Theater- 5 Fridays Concert Series Voices of Change: The Songs of Bob Dylan Friday, October 2 from 5 to 7pm outdoors on the Tilly Stage at the Maloney Plaza. An all-star group of Addison County and Vermont musicians celebrates the songs of Bob Dylan.The Songs of Bob Dylan brings together an all-star lineup of Addison County and Vermont musicians for a powerful outdoor celebration of one of America’s greatest songwriters

*PhotoPlace Gallery-Opening night Gala: Composed A Collaboration with Texas Photographic Society Juror: Brian Finke Exhibition: October 2 – October 31, 2026

*Swift House Inn for Serena Kim DJing from 6-10pm, Bar open from 5.00pm!

*Cookie Love open until 8pm

Buy Again Alley- open until 6pm: pop in to jump start your Spooky Season shopping on First fridays! 

*The Vermont Book Shop

Marquis Cinema-showing Digger with Tom Cruise   

*Retro Realm & Green Peppers until 9pm–Green Peppers will be open until 9pm and Retro Realm until 10pm. Running two specials for dine in or takeout!

• Sparrow Art Supply-usual  hours and Spotlight @ Sparrow exhibit featuring Susan Bruhl                                                                    *Flora/Next Door specials available at FLORA. See in store for details                                                                                                     *The Middlebury Shop-sale rack!

• Adagio Chocolates-will be open and serving Molten Chocolate!                                                                                                                   *Cobweb Antiques  

• Parlour 

• The Herbal Connection (Route 7 South) — Open late                                                                                                                                                  
• Danforth Pewter

• Stone Mill- TBD 

• Edgewater Gallery open late on Merchant’s Row     

• Middleton 

*Vermont’s Own

Plus Sabai Sabai, Taste of India, Crooked Ladle, Mr Ups, Mad Taco, The Middlebury Inn, Rosies, Fire & Ice and Two Brothers are open and waiting for you!

Come wander, sip, shop, and connect. See you downtown 💛 

Activities and events are rolling in all the time so be sure to check back on the website and The Addison Independent for latest updates!  This list will continue to be updated as we hear from local businesses and establishments. (If you’re a Middlebury store and haven’t replied yet—send us a quick message to [email protected] and we’ll include you in all our socials!)

Our goal is clear: to be a town known for sipping and shopping, grabbing something delicious, and running into your neighbors and friends downtown. A place where people come out not just to buy things—but to see one another and support the local businesses that support us all. 

READ ABOUT our very first “FIRST FRIDAY” HERE