Martha’s Vineyard, Massachusetts
Oak Bluffs Bar Crawl









Martha’s Vineyard History Tour and Oak Bluffs Bar Crawl

from $8 per person


Looking for an unforgettable adventure that blends history, culture, and fun in one epic experience? Look no further than our Martha’s Vineyard History Tour and Oak Bluffs Bar Crawl, the ultimate way to discover the hidden gems and iconic landmarks of this charming Martha’s Vineyard town!

You and your team will explore the history of the Vineyard—from the bustling Circuit Ave to the iconic Gingerbread cottages, the serene Ocean Park, and the legendary Flying Horses merry-go-round.

Your tour kicks off at the Ocean Park Bandstand, where you’ll embark on a journey through the rich history and culture of Oak Bluffs—finishing off your crawl with a refreshing ocean view brew 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 Martha’s Vineyard Bar Crawl and Oak Bluffs History Tour is the perfect adventure for you!

Book your tickets now and come explore the charming town of Oak Bluffs!

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 Martha's Vineyard!

If you’re looking for a peaceful escape from the hustle and bustle of city life, Martha’s Vineyard should be on your travel list. Located just off the coast of Massachusetts, this charming island is known for its beautiful beaches, quaint towns, and laid-back atmosphere. Whether you’re looking to relax on the beach, sample fresh seafood, or explore historic landmarks, Martha’s Vineyard has something for everyone.

One of the island’s biggest draws is its stunning natural beauty. With over 100 miles of coastline, Martha’s Vineyard boasts some of the most scenic beaches in the country. From the soft sands of South Beach to the rugged cliffs of Aquinnah, there’s no shortage of breathtaking vistas to discover.

In addition to its natural beauty, Martha’s Vineyard is also rich in history and culture. Visitors can explore historic sites like the Gay Head Lighthouse, the Island Alpaca Company, and the Martha’s Vineyard Museum, or take a stroll through down Circuit Ave in Oak Bluffs to shop, eat, or enjoy many of the local beers that make island living worth every second of your summer vacation!

Explore the Best Spots in Martha's Vineyard

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

The Best Times to Explore Martha's Vineyard

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:

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

Ocean Park
Flying Horses Carousel
Circuit Ave
Back Door Donuts
Gingerbread Cottages