You drink. We drive. Drink your way through Salem in October aboard a party trolley! Skip the bumpa-to-bumpa traffic and lines!About this Event
You drink. We drive.
Drink your way through Salem on Friday, October 2nd aboard a party trolley! Skip the bumpa-to-bumpa traffic, crazy ride-share rates, early as fuck train departure times, and bar lines, and raise some spirits this Halloween season!
Mobsters & Lobsters and Masshole Social Club team up to bring you an adults-only roundtrip trolley party from Boston to Salem!
We'll pick you up in Boston at 6 PM and drive directly to downtown Salem. Our Masshole tour guide will educate you on Salem's rich history—witch trials, pirates, robberies, brothels, murders, and more—while you pregame on the way. We'll arrive to Witch City around 7 PM.
When we're not driving your drunk ass around, we'll drop you off where you want to go along our route to explore our recommended bars and restaurants on your own. You'll have time to eat, drink, shop, take pictures, hit the Halloween festivities, or wander off and make some questionable decisions of your own.
Whenever you want to get back on the trolley, just wait for us to pull up at one of our designated hop-on-hop-off stops.
Just make sure to meet your designated driver at our final pickup spot at 1 AM to head back to Boston.
The Night at a Glance
6:00 PM — BOSTON PICKUP
BYOB. Get your ass on the trolley. We're headed to Salem!
7:00 PM — SALEM
Stay on the trolley or get dropped off at one of our central hop-on hop-off stops. The choice is yours throughout the night. Your tour guide is prepped to give you a Salem history lesson, a bottle of water, song recommendation, or a scolding.
1:00–2:00 AM — BACK TO BOSTON
Get back on the trolley! Your designated driver's driving your ass back to Boston.
WHAT YOU'RE GETTING
- ? Round-trip trolley transportation from Boston to Salem
- ? BYOB pregame and guaranteed place to party
- ? Convenient hop-on-hop-off stops throughout Salem
- ? 6-Hours of Salem's October nightlife and Halloween festivities
- ?️ Freedom to explore Salem on your own
- ? An adults-only group experience
- ? Designated driver
WHAT YOU'RE NOT GETTING
Crazy ride-share prices.
An 11 PM leave time to catch the next train back to Boston.
A two-hour walking tour where somebody whispers about ghosts.
A bus full of people who don't know how to have fun.
21+ only. Valid government-issued photo ID required.
Food and drinks are not included in the ticket price.
THE IMPORTANT STUFF
Date: Friday, October 2, 2026
Boston pickup: 6:00 PM
Pickup/Dropoff Location: 296 State Street, Boston, Massachusetts
Return to Boston: Approximately 2:00 AM
Duration: Approximately 8 hours
Age: 21+
Private Trolley Charters — Inquire
Itinerary and timing may change slightly due to traffic, weather, site access, or day-of conditions.
Presented by Masshole Social Club
The Commonwealth of Bad Decisions
Agenda
?: 06:00 PM
Pickup
Info: 296 State Street, Boston, Massachusetts
?: 07:00 PM - 01:00 AM
Witch City Salem
Info: Do your thing! Check out our bar and restaurant recommendations, go shopping, get a tarot reading, go to a haunted house... the fuck do we care?!
?: 02:00 AM
Drop Off
Info: 296 State Street, Boston, Massachusetts
Event venue
296 State St, 296 State Street, Boston, United States
Concerts, fests, parties, meetups — all the happenings, one place.