Middlebury businesses are excited to keep their doors open late on the First Friday of each month! A beautiful mix of late-night shopping, pop-ups, art, music, food, galleries, cocktails, karaoke, community, and summer energy all across downtown Middlebury. Here’s a little taste of what’s happening:

 NEXT FIRST FRIDAY JUNE 5…✨✨ 🎉  🎉✨  

* Little Seed return 5-8pm “ADULT RECESS” with wine by Lincoln Peak Vineyard and snacks by Little Seed

*Henry Sheldon Museum Join contemporary artist Luciana Frigerio and Time Keeping curator Kelly Hickey for a special gallery talk exploring the exhibit and Frigerio’s intricate series, Clockworks.5.30pm-6.30pm

*Listen to In Good Company on the Henry Sheldon Porch with Bill Vitek, Vanessa Dunleavy and friends  5-7pm. Kindly sponsored by the National Bank of Middlebury. 

*PhotoPlace Gallery — Open late/gallery viewing of PORTALS: NEW PERSPECTIVES Opening Reception 4-7pm

*Town Hall Theater will host the first of the FREE Five Fridays Concert Series in its Maloney Plaza on the Tilly Stage. This live music series will host food offerings and a bar. June 5: Dwight + Nicole Band. Genre-defying Dwight Ritcher and Nicole Nelson’s musical roots connect to blues, R&B, and soul with a little roots rock, alternative, and Americana sprinkled in. 

• Stone Mill — a return of the SPRIG WINE BAR  open late with music from Deep Think on the porch 6-8pm

• Edgewater Gallery (Main Street + Merchants Row) — Open late, exhibiting TO BELONG, a new body of work by Rory Jackson

• Haymaker — Late-night pasta pop-up from 5pm (the only one this month!), handmade pasta, fresh buns, specialty cocktails & drinks (boozy + non-boozy), followed by karaoke night 6-9pm with a professional setup-bring your kids,  friends, family and appetite, and your best ( or worst!) karaoke choice! No cover fee, no reservations, just come as you aregrab a plate, and take the mic (or cheer from the sidelines!)    

*Swift House Inn for Serena Kim DJing from 6-10pm “First FRIDAY Fancy! 

• Middleton — Open late…get fancy at Middleton before heading over to SWIFTHOUSE with Serena Kim! 

Wander downtown and pop into:

*The Vermont Book Shop for late-night browsing… Retro Realm open until 10pm plus Green Peppers until 9pm; 

• Sparrow Art Supply — Open until 5:30pm (possibly 6pm) with their “Onesie/Twosie Sale” featuring special items with only one or two left in stock before they disappear forever!                                                                     *Flora — Open late with $5 beverages + $5 pre-rolls                                                                                                         *The Middlebury Shop — Open late with a special sale rack
• Adagio Chocolates — Details TBD                                                                                                                            *Shiretown Marketplace — Pop-up TBD-WATCH THIS SPACE! 

*Cobweb Antiques — Hopefully opening late

• Parlour — Open late
• The Herbal Connection (Route 7 South) — Open late
• Vermont’s Own — Open late with special samples as well as the favorites                                                                                                                                                         *
• Danforth Pewter — Open late with 20% off purchases of $75+ (some exclusions apply)   

 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 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. There’s also an important Middlebury Money piece we’re eager to rebuild. With so many new faces in town, we realize not everyone is familiar with our unique local currency. Over the coming months, we’ll be reintroducing this concept—because keeping dollars local means strengthening our local economy and creating the kind of vibrancy we all want to be part of.

READ ABOUT our very first “FIRST FRIDAY” HERE