Ugly Sweater Holiday Trivia Crawl of Annapolis

Tours & Crawls of Annapolis and Baltimore

Zerve Seller: GhostTours
Activity #4075

This tour runs during the Christmas season. However, we run tour year round. Check our calendar for the next available tour!

You may view a calendar of other activities from GhostTours.
Or for more information, please contact GhostTours.


Do you love trivia? What about ugly Xmas Sweaters or holiday costume? Do you enjoy drinking? How about Holiday movies, TV specials and interesting historical tidbits about the various holidays? What if we combined them all together into one super fun evening?

Well, it's your lucky day, we have done just that! Come on out and enjoy a fun-filled night on our Ugly Sweater Holiday Trivia Pub Crawl!
Guests are encouraged to come in costume for this pub crawl! Put on your favority Ugly Holiday Sweater or come as the Jolly Fat man himself! Perhaps a naughty Mrs. Claus , the traditional Mrs. for the more inhibited or maybe one of Santa's little helpers on this rip-roaring holiday party crawl!

On this holiday pub crawl, we will be:
  • Visiting numerous taverns
  • Enjoying festive holiday cocktails and seasonal artisan beers 
  • Singing raucous carols from our "Naughty Xmas Carol Songbook" (to be supplied to each guest)
Need costume ideas? Be original and have fun! Break out your favorite Santa suit, Hot Elf outfit, Gift wrap yourself, Christmas Pajamas, dress as a Xmas Tree, Redneck Santa, a Trailer Park or a Slutty Mrs. Clause (again, yes please!) Whatever your twisted imagination can muster!

For our Jewish friends, come as a Dreidel, Hanukkah Harry, Judah Maccabbee or even as Gelt! "Hey Baby, wanna play "hide the Afikoman!" (I know, Passover)

Feeling timid? How about an ugly Xmas Sweater or a Cheesy Holiday Tie with a Santa Hat!

Our goal for the evening is to have a blast, entertain the fun-minded and offend the lame!

Naughty or Nice, come crawl with Santa!

What Is Not Included?

As much as we love drinking and hate being the Grinch, drinks are NOT included...You're on your own for those! While Santa told us that buying drinks for our crawlers is the Express Lane to the "Nice List", our insurance company Scrooges beg to differ...Sorry!

Guide & Bartender gratuities are not included

Get out of jail free cards are not included - Be smart, don't drink & drive!

Meeting Location

The Maryland Inn (Annapolis, MD) (Exact meeting location details will be provided immediately upon purchase of tickets.)
What is a pub tour/crawl?
The term "pub crawl" originated in England where, much like downtown Annapolis, small pubs and taverns are within walking distance of one another. Partygoers could go from one tavern to the next stopping for one drink at each establishment. You can imagine that by the end of the evening, some of the folks were "crawling" rather than walking! In this particular case, we will be sampling a variety of locally produced craft-brewed beers along the way!
Do I need to buy tickets in advance?
Yes, advance ticket purchase is required as tours do sell out. Any remaining tickets not sold 30 minutes prior to each tour are available for walk-up purchase on a space-available basis only. Advance purchase is highly recommended to ensure your participation.
Does my ticket include drinks?
NO! Your ticket guarantees your spot on the tour, lets you hear all our great stories, and provides you with a cool glow-in-the-dark bracelet to impress all your friends and identify you as a "crawler" for the duration of the evening. The ticket price does not include drinks - but some bar do offer a drink special to our guests, season dependent. Please bring extra money to purchase drinks along the tour route! Although most of our stops will accept credit cards, cash is preferred as it moves much faster.
What if I dont want to "crawl"?
Rest assured; neither crawling nor drinking is required on this tour. Our goal is to provide you with a different evening of entertainment, which may include the liquid spirits of this world and/or of the historical spirits of our storied past!
Does the tour happen rain or shine?
Yes, the tour runs in all weather unless it's dangerous. If we cancel the event, participants may reschedule for a future tour .
What should I wear?
Be sure to wear somewhat comfortable walking shoes. Dress appropriately for the weather (if it's raining we highly recommend raincoats and/or umbrellas). Please dress appropriately, as some of the bars in Annapolis do have dress codes. Shoes and shirts are required in all cases. Tank tops and cut-offs for men are not permitted in some establishments. We are not responsible if your attire does not conform to an establishment's dress codes.
What if I do not want to dress up in a costume? Can I still come?
While you will definitely be berated by your Santa-loving peers if you choose to not wear a costume, we will not turn you away. With that said, we strongly encourage you to avoid being deemed the Scrooge of the evening and put on some sort of holiday attire, whether that be an ugly Christmas sweater, a cheesy holiday tie, or a traditional Santa hat!
Is food available on the tour?
On our regular, open registration pub crawls, we do not provide food and are generally not at each bar long enough for you to order food. But, if you are starving, I'm sure something could be worked out with the bartender....However, if you are booking custom private tour for a group, we can likely work with you and some of the bars that we visit to provide appetizers or other snacks if you'd like.
Do I really need to bring ID? I'm way older than 21...
ABSOLUTELY! All guests must be 21+ to attend! We are not responsible if you are unable to gain entry into one of the taverns for failing to do so!
I don't want to be around a bunch of drunken "barely legals!" What ages come on your tour?
Good question - obviously to come on the tour, you must be over 21; however, our groups are usually very mixed. We've hosted 21st birthday parties as well as 50th birthday parties and older (We've even taken out the Red Hats...apparently tea isn't the only thing these ladies drink!). If you have a large enough group to make it cost effective (or if money is no object), you can always book a private tour. In the past, guests of all ages have mingled on the crawl and had a great time.
Can we bring our own booze or carry cocktails from bar to bar?
No! As much as we would love to let you, Maryland law is pretty specific on both of these points. And the bars enforce them rigidly! This means no flasks, no bar-noculars, no pocket beers for the road, and no hiding a bottle in your wife's cleavage and then pulling it out at the next bar (they were huge, and it was quite an impressive feat). No outside alcohol is permitted...period, no exceptions. No drinks may leave the bar...period, no exceptions.
May I smoke on the Pub Crawl?
That is totally at your discretion. However, please be advised that Maryland law prohibits smoking inside any public building, and that includes restaurants and bars. Smokers must indulge outside in approved areas. Sorry, not our call.
Can we bring cameras or video equipment?
Sure!!! How else are you going capture ghosts or show all your Facebook friends how cool a town Annapolis is and how much fun our Pub Crawls are! So have fun, and good shooting!
Is there any reason a tour won't go out?
If there are less than 3 guests for a tour or in unsafe conditions we may postpone or cancel a tour. We would of course reschedule your tour, or refund your ticket purchase.
If I am running late for the tour, will you wait for me?
We must start the tour on time because our other guests do not want to wait. If you are running late, please let us know (you will be provided contact information upon purchasing your tickets). Please give yourself plenty of time to get to the tour and find parking!
Do we go inside buildings during the tour?
But of course! How else would we get drinks!
Which bars do we visit?
Our route varies depending on the season, special events in Annapolis, bar availability, beer availability and the whim of our tour guides. We have visited Galway Bay, Harry Brownes, Sly Fox Pub, Drummer's Lot at the Maryland Inn, Castlebay, Federal House, Rams Head Tavern, Dock Street Bar & Grill and Middleton Tavern. In short, whoever has the best beers available on any given night! We will go to four bars on each tour, but specific route information is generally not available until the moment we depart.
How does it actually work?
On this holiday pub crawl, we will be visiting numerous taverns, enjoying festive holiday cocktails and seasonal artisan beers, and singing raucous carols from our "Naughty Xmas Carol Songbook" (to be supplied to each guest). Best of all, we will be doing it all in our favorite naughty holiday costumes!
What is the Naughty Xmas Carol Songbook and can I take it home with me?
Naughty Santa's Songbook is a collection of twisted, risqué and downright dirty versions of some of our most beloved Holiday Carols. Not for the easily offended! You can take it home, but prefer you leave them with your guide, so that the next group may recycle them and so on. Saves on wasted paper and makes us more green!
Is tipping acceptable or required?
That is totally at your discretion. Tipping is acceptable, but not required. We expect our guides to be highly professional, well-trained, and to entertain you regardless of potential gratuities. Many of our guests appreciate good service and choose to reward it, and the guides are always grateful. The same applies to the bartenders and servers at the bars we visit.
How long (distance) is your Pub Crawl?
It depends on which route we take but in most cases the entire tour is less and half a mile, as you usually only walk short distances between bars. While far from strenuous, we do recommend that you wear comfortable walking shoes and dress for the weather!
Is the tour route wheelchair accessible?
Due to the nature of Annapolis and the fact that many taverns were built and established prior to the Americans for Disabilities Act, it may be difficult for someone in a wheelchair to attend the tour. On a private tour we can arrange a route that is wheelchair accessible. To inquire further, please contact us via the "Contact HistoricPubs" link.
Is there parking near the tour?
We recommend parking in one of the several parking garages in downtown Annapolis, as many meters only allow a maximum of 2 hours. However, meters are only in effect until 7:30pm. After that they offer free parking! Parking garage information will be provided to you upon purchasing your tickets.
Are gift certificates available?
Sure! Please contact us directly via the "Contact GhostTours" link to inquire about purchasing a gift certificate.
Can I setup a private tour?
Absolutely! Private tours are available! We can schedule group tours any night of the week, and at any time. $325 for up to 15 guests. $15 per additional guest (a $5 per guest savings). To arrange your group event, please contact us via the "Contact HistoricPubs" link.


Refund/Rescheduling Policy

Non-refundable, can be rescheduled with 24 hours notice.
Once purchased, tickets cannot be refunded. You may reschedule your tickets (subject to availability) only if you do so at least 24 hours in advance.

Weather Policy

Activity may be cancelled due to severe weather.
The activity usually runs in light rain and other moderate weather conditions, but the seller may cancel the activity up to an hour before the start time in the event of severe or unsafe weather conditions. If the seller cancels the event, ticket-holders will be allowed to reschedule tickets (subject to availability) or receive credit for a future event.

Other Policies

All participants must be ages 21 or up with valid ID.
Some of the stops on our pub crawl have age restrictions just to enter. Furthermore, please also note that some of the pubs may be noisy, and members of your tour group as well as patrons in the bars will be drinking, some heavily. For these reasons, guests must be ages 21 or up and have proper ID with them. Refunds will not be provided for those under age 21 or without sufficient ID.
We reserve the right to remove guests behaving improperly or who are overly intoxicated!
Out of respect for all of the guests on our tours, we reserve the right to remove guests from the tour when the situation dictates such action. While we prefer never to have to exercise this right, in the event that any of the members of your party are either behaving improperly or are too drunk, we will remove said offender(s) from the tour. No refunds if a guest is removed from our tour!
Please be advised...
Some of the Annapolis pubs can be noisy places, and members of your tour as well as patrons in the bars will be drinking, some heavily. If you think any of these factors may irritate or bother you, we would ask that you please consider taking one of our walking tours instead. Your comfort and enjoyment are our main concern! Have fun!


Tours & Crawls of Annapolis and Baltimore

The Pub Crawls of Annapolis are the creation of well-known and respected Annapolis tour operator and author Mike Carter, who has been enlightening and entertaining guests and locals alike since 2002.
His new book, co-authored with guide Julia Dray, Haunted Annapolis: Ghosts of the Capital City is on bookshelves and online (Amazon, B&, etc.) now!

For more than three centuries, travelers and locals alike have been quenching their thirst in Annapolis' many historic pubs and taverns.  From our founding fathers to pirate rogues,  anyone in need of food, drink or entertainment found their way into our many historic bars...and you can too!

Enjoy one of our guided two-hour pub crawls around the darkened streets of Annapolis and into some of our oldest and most infamous drinking establishments.  Join us for a Historic Pub Crawl and relax with a cocktail while hearing about our colorful past through the tales of our historic taverns.  Or for our beer minded guests...stay in the present while sipping the tasty suds brewed at some of our region's finest breweries on a Craft-Brewed Beer Tour!

His newest addition to the genre of evening entertainment in historic downtown Annapolis is the Twisted History Tavern Tour; combining history, murder, mayhem, sex and scandal with beer, wine and cocktails!

Drink in the history, crawl out the door!
Please call Zerve at
1 (800) 979-3370
to get more information or
book this activity now
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