Portland, Maine
Old Port Bar Crawl









Portland Maine History Tour and Old Port Bar Crawl

from $8 per person


Looking for an unforgettable adventure that blends history, culture, and fun—all in one epic experience? Look no further than our Portland Maine History Tour and Old Port Bar Crawl, the ultimate way to discover the hidden gems and iconic landmarks of this charming Maine town!

You and your team will discover Portland’s maritime history as you walk through the bustling working waterfront of the Old Port. This 2 mile walking experience takes about 3 hours to complete. It starts at Lobsterman Park, includes a walk on the waterfront, and finishes in the center of the Old Port neighborhood.

The tour kicks off at Lobsterman Park, where you’ll embark on a journey to the waterfront, exploring the rich history and culture of Portland—finishing off your crawl with a refreshing brew on Exchange Street, just a stone’s throw away from where you started.

Each tour is private. You and your team will work together to solve puzzles, and answer trivia questions, while competing with your friends for the top spot on our leaderboard! So, whether you’re a history buff, or a beer enthusiast, our Portland Maine History Tour and Old Port Bar Crawl is the perfect adventure for you!

Book your tickets now and come explore the charming history of Portland!

* Portland is a city that loves dogs, but some of bars on the tour may not allow Fido to join. We recommend leaving the pooch at home for this tour. Also, Old Port is full of cobblestone roads and awkward curb cuts making it a challenge in some places for strollers and wheelchairs. Please keep that in mind.

Meetup with Friends

Get your friends together

Get your friends together and create your team name on the app. From there, we’ll guide you through city and share some of its most interesting history as you learn and explore.

Explore the city

Explore the city

We’ve turned your smartphone into the city’s best tour guide! As you go, we’ll be asking you scavenger hunt questions you can answer by exploring your surroundings.

Work together

Work together

In addition to scavenger hunt questions, we’ve packed the tour with trivia questions and puzzles you’ll need to work with you team to solve—and earn points along the way.

Grab a few drinks

Grab a few drinks

No tour is complete without the bars! As you walk through the city we’ll guide you to a few of the best bars in town. Plan for 4-6 bars on each tour.

*Drinks not included

amazing race meets drunk history

Imagine the best parts of scavenger hunts, historic walking tours, and bar trivia all packed into a world-class adventure game—that’s Brews & Clues! Work together with your friends to solve trivia questions, discover hidden landmarks, and earn points while competing for the top spot on the Brews & Clues Leaderboard!

Amazing Race meets Drunk HISTORY

Imagine the best parts of scavenger hunts, historic walking tours, and bar trivia all packed into a world-class adventure game—that’s Brews & Clues! Work together with your friends to solve trivia questions, discover hidden landmarks, and earn points while competing for the top spot on the Brews & Clues Leaderboard!

There's a lot to love about Portland

If you’re on the hunt for an awesome New England destination, look no further than Portland, Maine. You won’t want to miss out on the incredible culinary scene here. We’re talking about seafood that’s out of this world! Picture succulent lobster rolls, creamy clam chowder, and briny oysters that will make your taste buds sing.

In Portland, they take their seafood seriously. You can savor the freshest catches straight from the Atlantic, expertly prepared and served in the city’s top-notch restaurants. But it’s not just about seafood. The culinary scene embraces the farm-to-table philosophy, so you’ll find a wide range of dining spots offering mouthwatering dishes made with locally sourced ingredients. Oh, and don’t forget to check out the craft breweries while you’re here. They serve up unique flavors and handcrafted beers that’ll leave you wanting more.

Whether you’re yearning for a relaxing beach retreat, a journey through history, or a foodie adventure, Portland, Maine has got you covered. The coastal beauty is simply breathtaking, and the city’s past is filled with fascinating stories. Soak up the seaside charm, dive into the intriguing history, and treat yourself to the unforgettable flavors that make Portland, Maine a destination like no other.

Explore the Best Spots in Portland, Maine

There’s a lot to love in Portland. Here’s a few spots you’ll visit on the tour.

The Best Times to Explore Portland

Anytime is a good time to get outside with friends, but the best time for a Brews & Clues tour is when all the bars are serving.


Always private

All of our bar crawl trivia tours are a private experience, just for you and your friends.


No time limit

Explore the city at your own pace. There's no tour guide rushing you to the next bar.


Start anytime

We're ready when you are. Buy your ticket today and start your tour anytime.



If you don't love your tour, quit by question 5 and we'll give you a full refund.

Any questions?

Meet at the starting location, create a team name, and log in with your team. The tour will guide you through the city while you explore historic landmarks, learn local history, answer trivia questions, and solve puzzles. As you go, you’ll be guided to some of the best bars in town!

Tours typically take 3-4 hours to complete, but every team goes at their own pace. There is no time limit. We encourage people to make a day of it and enjoy each location as long as they want without feeling rushed.

No drinks are included with the price of your Brews & Clues ticket. From time to time on the tour, we may recommend our local favorites, but ultimately it’s up to you to decide what (and how much) you drink along the way.

In order to answer some questions on your tour, you’ll be asked to go in and out of bars, pubs and tap rooms. Some of those places, depending on the time of day, may restrict entry to anyone under 21.

Absolutely. We designed Brews & Clues to work on any smartphone without the need to download an app. As long as you can get on the internet, you can access the tour.

We have several team sizes available for different groups of people. When you’re purchasing your tour choose the size that works for you.

No worries—drinking is not required on the tour. Whether you drink or not, the experience is designed as fun, interactive and challenging for everyone to enjoy. Even without a buzz, we’re confident that you’ll have a good time.  

We’ve built a help guide within the app if you have any questions as you go. If that doesn’t solve your problem, our team is always just an email away. Just shoot us a note at: support@brewsandclues.com

It was a lot of fun! You didn’t feel like it was nearly 3 miles long because the stops are nicely spaced out. You get to experience a lot of historical landmarks while enjoying some equally great bars and pubs! The trivia is fun and challenging with a few tricky questions 😉 We liked that it was self guided and we were able to go at our own pace.


2-person team




TOTAL: $48

Best Value


12-person team




TOTAL: $96


6-person team




TOTAL: $72

Lobsterman Park
Berlin Wall Monument
Customs House
Portland’s Freedom Trail
Portland City Hall
Exchange Street