Friday Nights at 20 Deep Winery – Wine, Live Music & Food Trucks
Apr
10
6:00 PM18:00

Friday Nights at 20 Deep Winery – Wine, Live Music & Food Trucks

Spring Patio Season: Live Music, Great Food, and Your Favorite Wines

Music: 6 – 8 PM | Free: No Cover | No Reservations: Just Show Up

Every Friday night this spring, 20 Deep Winery in Rochester, NY will be hosting free live music from local artists. Enjoy a glass of wine or cold beer, grab a bite from this week’s food truck, and settle in. Music will be inside the tasting room or out on the patio, depending on the weather. Either way, Friday nights at the winery are all about enjoying that exhale you’ve been waiting for all week.

April

Food trucks start rotating in

Date Artist Genre Food
Apr 3 River Lynch Rock, Americana, Blues Freddie's Pizza
Apr 10 Peter Ryan Country Reservoir Dogs
Apr 17 Noah and Jess of Ivy's Home Upbeat Folk, Americana, Pop Freddie's Pizza
Apr 24 Sam Warren of Dirt Turtles Folk, Rockabilly, Blues Freddie's Pizza

May

Patio season is here

Date Artist Genre Food
May 1 Stephen Morrell Pop, Rock, Country Pat's Pigs BBQ
May 8 Kenny Ende Pop, Rock Reservoir Dogs
May 10 Sunday Stunt Double Trio
Mother's Day
Pop, Rock, Funk, Soul 12 – 3 PM Special Mother's Day Food Lineup
May 15 Ed Iseley Folk, Blues, Soul Freddie's Pizza
May 22 Chris & Korie Rollin' Deep ROC
May 29 John Akers Eat Greek

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Bonsai Workshop with Gallea’s
Apr
16
6:00 PM18:00

Bonsai Workshop with Gallea’s

Slow down, get your hands dirty, and leave with something living.

Join us for a beginner-friendly Bonsai workshop led by the team at Gallea’s Tropical Greenhouse and Florist in Pittsford. This relaxing hands-on evening is a chance to unplug, learn something new, and enjoy a glass of wine while you work.

You’ll learn how to:

  • Plant, shape, and care for your own Bonsai tree

  • Understand the basics of the Japanese art of Bonsai

  • Take your tree home with you at the end of the night

No experience needed. Just show up, grab a glass, and give it a try.

Details:

  • Date: Thursday, April 16, 2026

  • Time: 6:00 PM – 7:30 PM

  • Location: 20 Deep Winery, Mendon, NY

  • Price: $65 per person

  • Instructor: Gallea’s Tropical Greenhouse and Florist, Pittsford, NY


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Friday Nights at 20 Deep Winery – Wine, Live Music & Food Trucks
Apr
17
6:00 PM18:00

Friday Nights at 20 Deep Winery – Wine, Live Music & Food Trucks

Spring Patio Season: Live Music, Great Food, and Your Favorite Wines

Music: 6 – 8 PM | Free: No Cover | No Reservations: Just Show Up

Every Friday night this spring, 20 Deep Winery in Rochester, NY will be hosting free live music from local artists. Enjoy a glass of wine or cold beer, grab a bite from this week’s food truck, and settle in. Music will be inside the tasting room or out on the patio, depending on the weather. Either way, Friday nights at the winery are all about enjoying that exhale you’ve been waiting for all week.

April

Food trucks start rotating in

Date Artist Genre Food
Apr 3 River Lynch Rock, Americana, Blues Freddie's Pizza
Apr 10 Peter Ryan Country Reservoir Dogs
Apr 17 Noah and Jess of Ivy's Home Upbeat Folk, Americana, Pop Freddie's Pizza
Apr 24 Sam Warren of Dirt Turtles Folk, Rockabilly, Blues Freddie's Pizza

May

Patio season is here

Date Artist Genre Food
May 1 Stephen Morrell Pop, Rock, Country Pat's Pigs BBQ
May 8 Kenny Ende Pop, Rock Reservoir Dogs
May 10 Sunday Stunt Double Trio
Mother's Day
Pop, Rock, Funk, Soul 12 – 3 PM Special Mother's Day Food Lineup
May 15 Ed Iseley Folk, Blues, Soul Freddie's Pizza
May 22 Chris & Korie Rollin' Deep ROC
May 29 John Akers Eat Greek

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Friday Nights at 20 Deep Winery – Wine, Live Music & Food Trucks
Apr
24
6:00 PM18:00

Friday Nights at 20 Deep Winery – Wine, Live Music & Food Trucks

Spring Patio Season: Live Music, Great Food, and Your Favorite Wines

Music: 6 – 8 PM | Free: No Cover | No Reservations: Just Show Up

Every Friday night this spring, 20 Deep Winery in Rochester, NY will be hosting free live music from local artists. Enjoy a glass of wine or cold beer, grab a bite from this week’s food truck, and settle in. Music will be inside the tasting room or out on the patio, depending on the weather. Either way, Friday nights at the winery are all about enjoying that exhale you’ve been waiting for all week.

April

Food trucks start rotating in

Date Artist Genre Food
Apr 3 River Lynch Rock, Americana, Blues Freddie's Pizza
Apr 10 Peter Ryan Country Reservoir Dogs
Apr 17 Noah and Jess of Ivy's Home Upbeat Folk, Americana, Pop Freddie's Pizza
Apr 24 Sam Warren of Dirt Turtles Folk, Rockabilly, Blues Freddie's Pizza

May

Patio season is here

Date Artist Genre Food
May 1 Stephen Morrell Pop, Rock, Country Pat's Pigs BBQ
May 8 Kenny Ende Pop, Rock Reservoir Dogs
May 10 Sunday Stunt Double Trio
Mother's Day
Pop, Rock, Funk, Soul 12 – 3 PM Special Mother's Day Food Lineup
May 15 Ed Iseley Folk, Blues, Soul Freddie's Pizza
May 22 Chris & Korie Rollin' Deep ROC
May 29 John Akers Eat Greek

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From Garden to Jar — Herb Growing & Preservation Workshop
Apr
25
2:00 PM14:00

From Garden to Jar — Herb Growing & Preservation Workshop

Join Deb Jones, Certified Garden Master, for a hands-on workshop covering how to grow, harvest, and preserve fresh herbs at home. Learn what grows best in the region, when to plant, and simple methods for drying, freezing, and storing herbs to enjoy year-round.

Saturday, April 25 • 2–3 PM
Reservations required • Free to attend
Donations encouraged to support Hospeace House in Naples, NY.


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Sunday Bingo at 20 Deep Winery
Apr
26
11:00 AM11:00

Sunday Bingo at 20 Deep Winery

Sundays Just Got a Little More Fun

Sundays Just Got a Little More Fun at 20 Deep Winery

Free, family-friendly Bingo returns for one final date this year. Grab pizza, pour a glass of wine, and play for prizes for both kids and adults.

Two sessions available — pick the time that works best:
April 26 • 11 AM – 1 PM
April 26 • 3 PM – 5 PM

Five rounds of bingo with prizes including treats for kids, wine, glasses, pizza, and more. Freddie’s Wood Fired Pizza will be on site from 12–4 PM, with wine, beer, and non-alcoholic options available.

RSVP Bingo is free, but let them know you’re coming so they can set up enough tables.
Questions? Call or text 585-204-7953 or email info@20deep.com.


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Plant Bingo at Hazlitt Red Cat Cellars
Apr
26
12:00 PM12:00

Plant Bingo at Hazlitt Red Cat Cellars

  • The Wine Chalet at Hazlitt Red Cat Cellars (map)
  • Google Calendar ICS

Gaia’s Greens brings Plant Bingo to The Wine Chalet for a fun, plant-filled afternoon. Play for a chance to win a variety of unique plants — with new prizes each event.

April 26 • 12 PM

10 rounds for $30 • All ages welcome

Approx. 1.5 hours

Tickets are limited and sold exclusively through Gaia’s Greens.


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Sip Into Summer
May
16
12:00 PM12:00

Sip Into Summer

Kick off summer in the Finger Lakes with Sip into Summer, a signature event hosted by the Canandaigua Lake Wine Trail! Join us on May 16th from 12–4 PM at Inspire Moore Winery for an afternoon of wine tastings, live music, delicious food, and interactive wine experiences.

Your $40 Taster Ticket is a fantastic value. It includes tastings from all nine Canandaigua Lake Wine Trail wineries, a total value of over $90 if purchased individually, plus full access to live music by Big Blue House, local vendors like Clover & Fox, Steve’s Tye Dye, Studio 119 with flash tattoos and permanent jewelry, WaterGlass Collab, and even a petting zoo. Food will be available for purchase, including wood-fired pizza from Inspire Moore Winery.

Test your palate in a blind tasting for a chance to win two 2026 Passports, and attend meet-the-winemaker seminars to learn tips and insights from the winemakers themselves.

Taster Ticket - $40

For adults 21+ who want to enjoy wine tastings or beer.

Companion Ticket - $10

For anyone 13+ who wants to enjoy the event without wine tastings or alcohol.

Children 12 and under are FREE

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Cousins Maine Lobster Rolls into 20 Deep
Sep
28
11:00 AM11:00

Cousins Maine Lobster Rolls into 20 Deep

Get ready for a treat! Cousins Maine Lobster is rolling into 20 Deep Winery on Sunday, September 28th, from 11 AM. to 6 PM. As seen on ABC’s Shark Tank, The Cousins Maine Lobster Food Truck is bringing their amazing lobster rolls along with a wide array of lobster delicacies. Pair these delicious bites with a glass of our wine for a truly delightful afternoon!

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Friday Nights at 20 Deep Winery – Wine, Live Music & Food Trucks (Copy) (Copy)
Sep
26
3:00 PM15:00

Friday Nights at 20 Deep Winery – Wine, Live Music & Food Trucks (Copy) (Copy)

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!

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Autumn Blooms Wood Flower Workshop with Petal & Timber
Sep
21
2:00 PM14:00

Autumn Blooms Wood Flower Workshop with Petal & Timber

Get into the fall spirit with a creative afternoon at 20 Deep. Join Petal & Timber for a hands-on workshop where you’ll craft beautiful, everlasting wood flowers perfect for autumn decorating.

No experience needed – our instructors will guide you step-by-step through creating your own sustainable wood flower arrangement. Whether you’re decorating for fall, making a unique gift, or just love a good DIY project, you’ll leave with gorgeous blooms that last forever (no watering required!).

Date: Sunday, September 21st
Time: 2:00 – 4:00 PM
Location: 20 Deep Winery, 187 Mendon Ionia Rd, Honeoye Falls, NY 14472
Cost: $44.52 per person
What’s included: All materials and instruction

Wine and beverages available for purchase. Limited spots available – register today!

Refund Policy: Full refunds available up to 7 days before the event.

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Drag Brunch at 20 Deep Winery
Sep
14
11:00 AM11:00

Drag Brunch at 20 Deep Winery

Get ready for an unforgettable Sunday Funday! Join us for a fabulous drag brunch featuring Rochester’s most talented queens, delicious brunch by Madeline’s Catering, and mimosas at 20 Deep winery.

Sip, savor, and be entertained as our performers serve up comedy, lip-syncs, and all the glamour you can handle. Come hungry – Madeline’s Catering is bringing their incredible brunch buffet. Whether you’re celebrating a special occasion or just living your best weekend life, this is the can’t-miss event of the season!

Date: Saturday, September 14th
Time: 11:00 AM – 1:00 PM
Location: 20 Deep Winery
Tickets: TBD
Includes: Brunch buffet by Madeline’s Catering and entertainment

Full bar available, including mimosas, wine, beer and n/a alcoholic beverages. 21+ event.

Limited seating – grab your tickets before they sell out!

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Friday Nights at 20 Deep Winery – Wine, Live Music & Food Trucks
Sep
12
3:00 PM15:00

Friday Nights at 20 Deep Winery – Wine, Live Music & Food Trucks

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!

View Event →
Friday Nights at 20 Deep Winery – Wine, Live Music & Food Trucks
Sep
5
3:00 PM15:00

Friday Nights at 20 Deep Winery – Wine, Live Music & Food Trucks

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!

View Event →
Labor Day Weekend Fiesta at 20 Deep
Aug
30
12:00 PM12:00

Labor Day Weekend Fiesta at 20 Deep

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.

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Donna The Buffalo Live at Inspire Moore Winery
Aug
22
5:00 PM17:00

Donna The Buffalo Live at Inspire Moore Winery

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.

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Friday Nights at 20 Deep – Wine, Music & Food Trucks
Aug
22
3:00 PM15:00

Friday Nights at 20 Deep – Wine, Music & Food Trucks

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.

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🎉 Trivia Night at 20 Deep Winery
Aug
21
5:00 PM17:00

🎉 Trivia Night at 20 Deep Winery

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

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Cousins Maine Lobster Rolls into 20 Deep
Aug
17
11:00 AM11:00

Cousins Maine Lobster Rolls into 20 Deep

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.

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Pilates Pop-Up with Julia Tiberio (Copy)
Aug
17
10:00 AM10:00

Pilates Pop-Up with Julia Tiberio (Copy)

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

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Friday Nights at 20 Deep – Wine, Music & Food Trucks
Aug
15
3:00 PM15:00

Friday Nights at 20 Deep – Wine, Music & Food Trucks

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.

View Event →
Friday Nights at 20 Deep – Wine, Music & Food Trucks
Aug
8
3:00 PM15:00

Friday Nights at 20 Deep – Wine, Music & Food Trucks

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.

View Event →
Friday Nights at 20 Deep – Wine, Music & Food Trucks
Aug
1
3:00 PM15:00

Friday Nights at 20 Deep – Wine, Music & Food Trucks

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.

View Event →
Friday Nights at 20 Deep – Wine, Music & Food Trucks
Jul
25
3:00 PM15:00

Friday Nights at 20 Deep – Wine, Music & Food Trucks

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.

View Event →