RICHMOND'S BIGGEST CARYTOWN SINGLES HALLOWEEN BAR CRAWL 2026 (FRIDAY)

Granby Street • Grain Rooftop • Waterside District
About this Event
🎃 RICHMOND'S BIGGEST CARYTOWN SINGLES HALLOWEEN BAR CRAWL 2026 👻

Carytown • West Cary Street • Richmond

One Night. Four Bars. One Massive Halloween Singles Crawl.

🍹 Grab a drink.
🎃 Put on your costume.
🏙️ Take over Carytown.
💘 Meet Richmond singles.
👻 Maybe find your boo.

RICHMOND'S BIGGEST CARYTOWN SINGLES HALLOWEEN BAR CRAWL 2026
SATURDAY • OCTOBER 31, 2026

📍 CARYTOWN • RICHMOND, VIRGINIA

Meet • Match • Mingle • Crawl

Come single. Come in costume. Find your boo. 👻💘

🎃 ONE NIGHT. CARYTOWN. WEST CARY STREET. MULTIPLE BARS.

Halloween night is taking over Carytown.

We're bringing together singles, costumes, cocktails, music and Halloween nightlife for one massive singles bar crawl through one of Richmond's most recognizable entertainment districts.

Put down the dating apps.

Put on a costume. Grab a drink. Meet someone in real life.

Come alone.
Come with your single friends.
Come in costume.
Meet someone completely unexpected.

💘 Meet. Match. Mingle. Crawl.

🍹 THE OFFICIAL CRAWL ROUTE

Halloween night starts at New York Deli, where attendees will meet the group, check in and receive their crawl wristbands.

From there, we're moving together along West Cary Street:

🎃 STOP #1 — NEW YORK DELI

8:00 PM–9:00 PM

📍 2920 W. Cary Street

OFFICIAL CHECK-IN & WRISTBAND PICKUP

This is where your Halloween night begins.

Arrive starting at 8:00 PM, check in with the group, receive your crawl wristband, grab your first drink and start meeting other Richmond singles.

Get there early. Meet the group. Check out everyone's costumes and get ready for the crawl.

New York Deli also features its Rockaway Beach Rooftop Tiki Lounge, giving us a great place to kick off Halloween night.

🍸 STOP #2 — THE JASPER

9:00 PM–10:00 PM

📍 3113 W. Cary Street

Next we're heading down Cary Street to The Jasper.

Grab a cocktail and introduce yourself to someone you haven't met yet.

This portion of the night is all about cocktails, conversation and mingling before the Halloween crowd gets even bigger.

🎸 STOP #3 — RIPPLE RAY'S

10:00 PM–11:15 PM

📍 3123 W. Cary Street

Now we're turning up the energy.

Ripple Ray's brings a more energetic neighborhood-bar and live-music atmosphere to the crawl.

Grab another drink, meet more crawlers and keep the Halloween party moving.

🔥 STOP #4 — HOME SWEET HOME

11:15 PM–LATE

📍 3433 W. Cary Street

Our fourth stop takes us farther down Cary Street to Home Sweet Home.

This becomes our late-night Carytown meetup destination.

Drinks. Costumes. Singles. Halloween energy.

🌙 MIDNIGHT–2:00 AM — CARYTOWN HALLOWEEN FINALE

After midnight, stay out and enjoy Halloween night throughout Carytown.

We'll continue sending crawl updates and meetup information to registered attendees as the night develops.

Stay out. Meet somebody. Find your boo. 👻💘

🗺️ YOUR HALLOWEEN ROUTE

8:00 PM — NEW YORK DELI
⬇️
9:00 PM — THE JASPER
⬇️
10:00 PM — RIPPLE RAY'S
⬇️
11:15 PM — HOME SWEET HOME
⬇️
MIDNIGHT–2:00 AM — CARYTOWN HALLOWEEN FINALE

🎃 WHAT TO EXPECT

🎃 Halloween costumes
🍹 Multiple Carytown bars
🏙️ West Cary Street bar hopping
🍸 Cocktails & drinks
🎶 Music & Halloween nightlife
💘 Singles-focused social experience
🤝 Opportunities to meet new people
📱 Crawl updates & meetup instructions
❤️ Optional personalized introductions
👑 VIP matchmaking & concierge options
🔥 Late-night Halloween atmosphere

Costumes are highly encouraged.

Go scary. Go funny. Go creative. Go ridiculous. Go all out.

It's Halloween.

💘 COME ALONE — SERIOUSLY.

You don't need a date.

You don't need a group.

And you definitely don't need to convince five friends to come with you.

This event is specifically designed for singles to meet other singles.

Coming alone can actually make it easier to meet people.

Walk into New York Deli. Find the group. Pick up your wristband. Grab a drink. Introduce yourself.

And on Halloween, everyone already has the easiest conversation starter:

"What are you supposed to be?" 👻

⚖️ A BALANCED SINGLES EXPERIENCE

We aim to create a strong mix of singles and maintain a balanced experience whenever possible.

Attendance and ratios naturally vary, so an exact gender ratio cannot be guaranteed.

🎟️ TICKET OPTIONS
🎃 General Admission Crawl Pass — $10

Includes:

• Admission to the organized singles crawl experience
• Event check-in & wristband pickup
• Crawl instructions and meetup information
• Open mingling with participating singles
• Access to the Halloween Singles Crawl community
• Opportunity to meet singles throughout the night

Food and beverages are purchased separately.

RSVP required. Capacity is limited.

💙 VIP Dating Pass — $25 | MOST POPULAR

Includes everything in General Admission, plus:

• VIP Dating Pass
• Matchmaking assistance throughout the crawl
• Help identifying singles you may be interested in
• Personalized introductions when available
• Priority dating support
• Ability to tell our team who you'd like to meet

See someone interesting?

Tell us. We'll help break the ice. 💘

✨ VIP+ Matchmaker Pass — $40

Includes:

• Everything in the VIP Dating Pass
• Personalized matchmaking intake
• Curated match recommendations
• Priority matchmaking assistance
• Priority introductions
• Enhanced matchmaking support
• Post-event match assistance when applicable

Perfect for singles who actually want to meet someone—not just attend another Halloween party.

💎 Diamond Matchmaking Concierge — $97 | LIMITED

Our highest-level Halloween matchmaking experience.

Includes:

• Everything in VIP+ Matchmaker
• Private pre-event matchmaking review
• Personalized match recommendations
• Highest-priority introductions
• Concierge-level matchmaking assistance
• Priority support during the event
• Private post-event follow-up and guidance

Availability is intentionally limited so our team can provide more personalized attention.

🌐 DMV DATING GROUP

We host singles mixers, dating events, matchmaking experiences, speed dating, nightlife events, brunches, bar crawls and social experiences throughout Virginia, DC, Maryland and beyond.

DMVDatingGroup.com

📌 IMPORTANT INFORMATION

This is a singles social and bar-crawl experience.

Food and beverages are not included with admission unless specifically stated. Guests purchase their own food, drinks and other items directly from each venue.

New York Deli is the planned starting/check-in location. Attendees should check their final event instructions before arriving in case the route or check-in arrangements change.

Potential venues listed on this page are not necessarily sponsors or confirmed participating venues. The route, timing, check-in procedures and participating destinations are subject to change.

Guests must comply with all venue policies, identification requirements, dress codes, capacity restrictions, cover charges and applicable rules.

21+ where required. Valid government-issued ID may be required.

Please drink responsibly and use rideshare, taxi, public transportation or a designated driver.

⚠️ MATCHMAKING DISCLAIMER

This event is designed to create opportunities for singles to meet and connect.

Our team can facilitate introductions and provide matchmaking assistance depending on the ticket purchased, but specific matches, romantic connections, dates or relationship outcomes cannot be guaranteed.

🎃 RICHMOND'S BIGGEST CARYTOWN SINGLES HALLOWEEN BAR CRAWL 2026 👻
SATURDAY • OCTOBER 31 • 8 PM–2 AM
CHECK-IN: NEW YORK DELI • 8:00 PM
CARYTOWN • WEST CARY STREET • RICHMOND, VA

Meet • Match • Mingle • Crawl

Come single. Come in costume. Find your boo. 👻💘