Join us for a relaxed, flavorful night featuring handcrafted pizza and live acoustic sets from local favorites. It’s the perfect pairing of great food, good music, and Finger Lakes summer vibes.

Looking for things to do in Rochester, NY on a Friday night? Unwind from the week and kick off the weekend with Friday Nights at 20 Deep Winery—where local wine, live music, and food trucks come together for a laid-back evening with friends and family. Whether you’re here for the wine, craft beer, live entertainment, or great food, we’ve got a spot waiting for you at our Rochester, NY winery.

What to Expect on Friday Nights at 20 Deep Winery

If this is your first time at 20 Deep Winery, or if you haven’t yet experienced a summer Friday night with us, here’s a glimpse of what awaits you during your visit.

• Rotating Food Trucks  – A new taste every week (see schedule below).

• Live Music – A lineup of local talent from 6 PM – 8 PM.

• Outdoor Seating & Games – Corn hole, Bocce Ball, Giant Connect Four & more.

• Cozy Fire Pit Seating – Blankets available for guests to use on cooler nights.

• Small-Batch Wines & Local Brews  – Exclusive wines available on tap and local beers to enjoy.

• Kid-Friendly Activities – A sandbox with toys (bring your own if you’d like!)

We Serve Wine, Beer & Non-Alcoholic Drinks

Enjoy a selection of red, white, and sparkling wines. We specialize in dry-style wines but also offer small-batch wines with a hint of sweetness for those who prefer something sweeter. In addition, we offer a rotating selection of local beers for non-wine drinkers and a variety of N/A drinks for guests of all ages.

📋 View Our Full Drink Menu: 20 Deep Menu

How to Plan Your Visit

We’ve got plenty of seating options—bistro tables on our covered patio, picnic tables and Adirondack chairs out on the lawn, and a cozy gas fireplace to gather around. While we have lots of spots to sit, busy nights can fill up fast, so feel free to bring a bag chair just in case.

Coming with a group? Reservations for 6+ are encouraged. Give us a call or text at 585-204-7953 to let us know you’re coming!

Join us for a relaxed, flavorful night featuring handcrafted pizza and live acoustic sets from local favorites. It’s the perfect pairing of great food, good music, and Finger Lakes summer vibes.

Make the most of your long weekend—kick off Labor Day with Latin rhythms, fresh kabobs, and a glass of our holiday sangria. Drop in for the noon dance lesson (or just watch), stay for live music from 1–3 PM, and relax on the patio with friends until 5. Space is open-seating; arrive early, grab your food, and let the fiesta begin.

Details

-Saturday August 30th, the winery will be open from 11a – 9p.

-Free Latin dance lessons (Salsa, Bachata, Merengue) provided by Rochester Dance from 12p – 1p

-Live music by Los Pajaritos, a Latin and Spanish band based out of Rochester NY led by Karson Bolaño will be playing music from 1p – 3p.

– Robb’s Kabobs will be serving Puerto Rican & Italian fusion cuisine from 1p – 5p

-We will be releasing our fall sangria + our full wine/beer menu will be available.

RSVP here so we can prepare enough food and space for all our guests.

Join us for a relaxed, flavorful night featuring handcrafted pizza and live acoustic sets from local favorites. It’s the perfect pairing of great food, good music, and Finger Lakes summer vibes.

Join Inspire Moore Winery for an incredible evening of live music featuring the return of Donna The Buffalo, with special guests Temple Cabin Band opening the show.

This summer concert under the pavilion includes:
– Live music
– Food trucks
– Local beer on tap
– Craft cocktails
– Wood-fired pizza
– Inspire Moore wines by the glass or bottle

Admission:
• $25 advance tickets
• $30 at the door
• Kids 8 and under are free with an adult

This is a rain or shine event. Please bring umbrellas and dress for the weather.
No outside food or beverages permitted.

Every Friday this summer, 20 Deep Winery hosts a laid-back evening of live music, local food trucks, and wine on tap. Enjoy lawn games, cozy fire pits, and a rotating lineup of small-batch wines, craft beers, and family-friendly activities. Music runs 6–8 PM—no reservations needed.

Thursday, August 21st Join us for a night of fun and friendly competition at Trivia Night, hosted by Game Night Rochester! Bring your crew and test your knowledge while enjoying wine, beer, delicious food truck eats. Reserve your spot now!

📅 Event Details:

• Date: Thursday, August 21st, 2025

• Trivia: 7:00 PM – 9:00 PM

• Say Cheese Please Food Truck: 5:00 PM – 8:00 PM

• Winery Hours: 11:00 AM – 10:00 PM

🎨 What to Expect:

• Say Cheese Please Food Truck – Serving up gourmet grilled cheese and comfort food from 5-8 PM

• Charcuterie & Snacks – Available for purchase all evening

• Wine, Beer & NA Beverages – Available by the glass or carafe

• Prizes – Top trivia team wins something great!

📝 How to Participate:

• Form a Team – Up to 8 people per team

• Reserve Your Spot – Pre-registration is recommended to guarantee a table (Grab Your Spot Before It’s Gone!)

• Arrive Early – Come early to grab dinner from the food truck and get settled before trivia starts at 7 PM

Not playing trivia? No problem! You’re still welcome to hang out and enjoy wine, food truck favorites — the winery is open to all.

This is your chance to break away, get a night out with your friends, and enjoy some time away from the annoying kids. Just relax, be present, and have a great time

The famous Cousins Maine Lobster Truck is pulling up to 20 Deep Winery on Sunday, August 17 from 11 AM to 6 PM! Featured on Shark Tank, this food truck serves up buttery lobster rolls, bisque, and other coastal favorites. Pair your bites with a glass of wine for the ultimate summer afternoon.

Join Julia Tiberio, Certified Fitness Instructor, for an energizing morning of movement in the beautiful vineyard setting at 20 Deep Winery. Start your Sunday with a dynamic pilates class. This outdoor event welcomes all fitness levels – whether you’re a seasoned pro or just getting started. After the event, relax and refuel with a mimosa or glass of 20 Deep wine.

Date: Sunday, August 17th
Time: 10:00 – 11:00 AM
Location: 20 Deep Winery outdoor space (weather permitting)
Cost: $20
Payment: Venmo @Julia-Tiberio (last 4 digits: 4400)
What to bring: Yoga mat, comfortable fitness wear, water bottle, and sweat towel

Space is limited. Reserve your spot by sending payment via Venmo with “20 Deep Pilates/Zumba” in the notes.

Questions? Contact Julia at juliaetiberio@gmail.com

Join us for a relaxed, flavorful night featuring handcrafted pizza and live acoustic sets from local favorites. It’s the perfect pairing of great food, good music, and Finger Lakes summer vibes.

Every Friday this summer, 20 Deep Winery hosts a laid-back evening of live music, local food trucks, and wine on tap. Enjoy lawn games, cozy fire pits, and a rotating lineup of small-batch wines, craft beers, and family-friendly activities. Music runs 6–8 PM—no reservations needed.

Join us for a relaxed, flavorful night featuring handcrafted pizza and live acoustic sets from local favorites. It’s the perfect pairing of great food, good music, and Finger Lakes summer vibes.

Every Friday this summer, 20 Deep Winery hosts a laid-back evening of live music, local food trucks, and wine on tap. Enjoy lawn games, cozy fire pits, and a rotating lineup of small-batch wines, craft beers, and family-friendly activities. Music runs 6–8 PM—no reservations needed.

Join us for a relaxed, flavorful night featuring handcrafted pizza and live acoustic sets from local favorites. It’s the perfect pairing of great food, good music, and Finger Lakes summer vibes.

Acquilano Wine Cellars in Canandaigua offers a vibrant lineup of live music throughout the summer. From jazz ensembles to acoustic sets, enjoy performances from talented local musicians while savoring their handcrafted wines. It's the perfect setting for a relaxing evening in the Finger Lakes.

Every Friday this summer, 20 Deep Winery hosts a laid-back evening of live music, local food trucks, and wine on tap. Enjoy lawn games, cozy fire pits, and a rotating lineup of small-batch wines, craft beers, and family-friendly activities. Music runs 6–8 PM—no reservations needed.

Join us for a relaxed, flavorful night featuring handcrafted pizza and live acoustic sets from local favorites. It’s the perfect pairing of great food, good music, and Finger Lakes summer vibes.

Acquilano Wine Cellars in Canandaigua offers a vibrant lineup of live music throughout the summer. From jazz ensembles to acoustic sets, enjoy performances from talented local musicians while savoring their handcrafted wines. It's the perfect setting for a relaxing evening in the Finger Lakes.

Every Friday this summer, 20 Deep Winery hosts a laid-back evening of live music, local food trucks, and wine on tap. Enjoy lawn games, cozy fire pits, and a rotating lineup of small-batch wines, craft beers, and family-friendly activities. Music runs 6–8 PM—no reservations needed.

Join us for a relaxed, flavorful night featuring handcrafted pizza and live acoustic sets from local favorites. It’s the perfect pairing of great food, good music, and Finger Lakes summer vibes.

Acquilano Wine Cellars in Canandaigua offers a vibrant lineup of live music throughout the summer. From jazz ensembles to acoustic sets, enjoy performances from talented local musicians while savoring their handcrafted wines. It's the perfect setting for a relaxing evening in the Finger Lakes.

Acquilano Wine Cellars in Canandaigua offers a vibrant lineup of live music throughout the summer. From jazz ensembles to acoustic sets, enjoy performances from talented local musicians while savoring their handcrafted wines. It's the perfect setting for a relaxing evening in the Finger Lakes.

Join us for a relaxed, flavorful night featuring handcrafted pizza and live acoustic sets from local favorites. It’s the perfect pairing of great food, good music, and Finger Lakes summer vibes.

Join us for a relaxed, flavorful night featuring handcrafted pizza and live acoustic sets from local favorites. It’s the perfect pairing of great food, good music, and Finger Lakes summer vibes.

Mark your calendar—Inspire Moore’s 18th Annual B4 Celebration is happening July 5th!

Join us from 11 AM to 5 PM for a full day of wine tastings, blues music, BBQ, and summer fun. We’ll have:
• Live music by Brian Burley and Big Blue House
• BBQ and axe throwing food trucks
• Wood-fired pizza and beer for purchase
• Free Blaufränkisch tastings
• Lawn games, sunshine, and good vibes

The party takes place outdoors under the pavilion—rain or shine.
Free admission until 5 PM. Come celebrate summer and 18 years of Inspire Moore!

Acquilano Wine Cellars in Canandaigua offers a vibrant lineup of live music throughout the summer. From jazz ensembles to acoustic sets, enjoy performances from talented local musicians while savoring their handcrafted wines. It's the perfect setting for a relaxing evening in the Finger Lakes.

Langhorne Slim returns to Inspire Moore Winery on June 28th, 2025 with opener Oscar Fargnoli! We will have food trucks, local beer on tap, our own wood fired pizza, cocktails, and of course WINE! NO OUTSIDE FOOD OR DRINKS PERMITTED, rain or shine, bring umbrellas, kids 8 and under free with an adult. Doors 5 PM. Music begins at 6 PM. Tickets $25/advanced, $30/door.

Join us for a relaxed, flavorful night featuring handcrafted pizza and live acoustic sets from local favorites. It’s the perfect pairing of great food, good music, and Finger Lakes summer vibes.

Acquilano Wine Cellars in Canandaigua offers a vibrant lineup of live music throughout the summer. From jazz ensembles to acoustic sets, enjoy performances from talented local musicians while savoring their handcrafted wines. It's the perfect setting for a relaxing evening in the Finger Lakes.