- Event Overview
About
Essex, VT
Ugly Sweater Pub Crawls
Essex’s Ugly Sweater Pub Crawl brings Baltimore County’s bar culture and Maryland holiday spirit to the holiday sweater tradition. The Eastern Avenue and the Essex downtown bar district have developed into a vibrant scene and on ugly sweater night the combination of the Chesapeake Bay working-class character, the Baltimore County community warmth, and the excellent local bars creates a holiday celebration with a Maryland character that is authentic, warm, and completely Essex.
Our Essex route moves through Eastern Avenue and the surrounding bar district, stopping at venues that represent the quality and character of what Essex’s bar scene has built. The ugly sweater competition in Essex draws on the creative energy of a Chesapeake Bay community with strong blue-collar heritage and the entries reflect that Maryland combination of crab house culture, Baltimore County pride, and genuine holiday warmth.
December in Essex is cold, typically ranging from 28 to 40 degrees at night. The Maryland winter is real and the Essex holiday decorations have the warm, community character of a Baltimore County neighborhood that values its working-class heritage. The bar community here has the genuine warmth and hospitality that defines Chesapeake Bay communities.
Our hosts manage the Essex route with local knowledge. Specials are confirmed, wristbands handle entry at every stop, and the ugly sweater contest brings Chesapeake Bay community creativity to the holiday season.
Event Detalis
Everything you need to know about the Essex Ugly Sweater Bar Crawl.
VIP Wristband
Largest Pub Crawl Event
Top Essex Ugly Sweater Bar Crawl
40,000+ Attendees
Thousands join the annual Essex Ugly Sweater Bar Crawl
100+ Participating Bars
Organized Event
- What's Included
What You Get With a Pub Crawl Ticket
Pub crawls for the biggest party holidays. Choose your event and join the party in 100+ cities across the USA.
Ugly Sweater Contest
The most outrageous sweater wins a prize.
Welcome Drink at Check-In
Included with your ticket.
Drink Specials at Every Stop
Exclusive holiday pricing throughout the route.
Official 2025 Wristband
One wristband for every venue on the crawl.
On-Site Hosts
Our team manages the route and the sweater competition.
VIP Entry at Select Venues
Priority access at participating bars.
Holiday Party Gear
Festive accessories at check-in.
Pub Crawl Route
The crawl covers the best bars in the city’s top bar neighborhood.
Participating Venues on the Pub Crawl Route
The 2026 Essex Ugly Sweater Bar Crawl route runs through State Street / Capitol Square. All stops within walking distance. Full lineup sent to ticket holders before the event.
How the Pub Crawl Works
Four simple steps to join the Essex Ugly Sweater Bar Crawl and start bar hopping.
Purchase at pubcrawls.com.
7:00 PM. Address with ticket confirmation.
Welcome drink, wristband, holiday gear. Route starts at 7:30 PM.
Hosts guide the group through venues all evening.
Event Agendas
Your complete Essex Ugly Sweater Bar Crawl timeline from check-in to after-party.
Frequently Asked Questions
Everything you need to know about the Essex Ugly Sweater Bar Crawl.
Where does the crawl start?
Essex MD. Exact address with ticket purchase.
What is the weather like?
Essex MD in December averages 28 to 40 degrees at night. Cold Maryland winter. Layer under your sweater.
Is there a dress code?
Ugly sweaters are the theme. The more outrageous the better.
What is included?
Welcome drink, wristband, drink specials, holiday gear, ugly sweater contest.
Group bookings?
Ten or more get priority entry. Contact pubcrawls.com.
Age requirement?
21 and over with valid ID.
Can I buy at the door?
Subject to availability. Buy in advance.
Is the event walkable?
Yes. All venues are within walking distance on the route.
