1. No results to show.
Explore Services
Join as a pro
Log in
  1. No results to show.
  1. No results to show.
Home
Explore Services
Sign up
Log in

The Tipsy Trolley

Top Pro

Contact for price
Scheduling
Budget

Responds in about 3 hours

Thumbtack Guarantee

If you hire this pro, you’re covered by a money-back guarantee. Learn more

If you hire this pro, you’re covered by a money-back guarantee. Learn more

About
Welcome to The Tipsy Trolley, Southeastern Michigan’s one-of-a-kind mobile bartending experience. Owned and operated by Jill and Ben Tolliver, we bring exceptional beverage service to events of all kinds. From weddings and corporate events to backyard celebrations and festivals, we deliver an elevated, stress-free bar experience that your guests will love. Whether you’re hosting in Metro Detroit, celebrating in Monroe, planning a wedding in Ann Arbor, organizing a corporate event in Jackson, or anywhere across Southeastern Michigan, The Tipsy Trolley brings the bar directly to you—with style, professionalism, and unforgettable drinks.
Overview

Current Top Pro

Hired 12 times

Serves Taylor, MI

Background checked

6 employees

1 year in business

Business hours

This pro hasn't listed their business hours.

Payment methods

This pro accepts payments via Cash, PayPal, and Venmo.

Services offered
Beverage types
Event type

Wedding reception

Birthday party

Special occasion

Cocktail party

Event vibe

Low key / casual

Formal / elegant

Upbeat / lively

Club scene

Projects and media
Projects and media
Reviews

Customers rated this pro highly for value, work quality, and professionalism.

Great 4.8

6 reviews

5

83%

4

17%

3

0%

2

0%

1

0%

Read reviews that mention:

pro avatar
Cora M.

Dec 18, 2025

•

Hired on Thumbtack

I wanted to select all options as they deserve all of them. The ladies who tended bar for us were amazing. Very quick at serving drinks, professional, kind, patient, brought a great setup, answered any questions our guests had regarding wine, very responsive to emails, and a great value. I highly recommend them for any event you have.

Details: 51 - 75 guests • Holiday party • Low key / casual • Private residence • Beer • Wine • Non-alcoholic beverages • Bartender will need to bring the bar • I'm flexible • Setup / cleanup

Bartending
pro avatar
Eboni R.

Dec 30, 2025

•

Hired on Thumbtack

The Tipsy Trolley was great! They showed up on time and completely set up everything! All I had to do was stock the bar as agreed upon and they took it from there! I got a lot of compliments on the bar, which is a direct reflection of the work of Jill and the Tipsy Trolley! We are a small nonprofit, and were hosting our first gala and she recognized that and gave us nothing but reassurance and support! I would recommend them 1000x #Superb

Details: 26 - 50 guests • Fundraiser • Formal / elegant • Private residence • Beer • Liquor / mixed drinks • Wine • Non-alcoholic beverages • Bartender will need to bring the bar • Tip jars not allowed • Setup / cleanup • Ice • Disposable cups • Coolers

Bartending
pro avatar
Sean M.

Jun 15, 2026

•

Hired on Thumbtack

We could not be happier with the services provided by Tipsy Trolley. They were great! Jill helped us come up with the menu and put together a shopping list. On the day of the event, they showed up early to setup and during the event were fun, professional and skilled. I would definitely use them again and recommend them to anyone that asks.

Details: 51 - 75 guests • Special occasion • Low key / casual • Private residence • Liquor / mixed drinks • Non-alcoholic beverages • Bartender will need to bring the bar • Tip jars allowed

Bartending
pro avatar
Shelley B.

Dec 1, 2025

I attended a party where the Tipsy Trolley was bartending. The signature cocktail was delicious and the atmosphere was so festive!
pro avatar
Dee S.

Dec 10, 2025

Tipsy Trolley really rocked !!!
Credentials
Background Check

Jill Tolliver

  • Loading

Related cost information

You might also like

Thumbtack
Consider it done.
Customers
Pros
Support
© 2026 Thumbtack, Inc.
Thumbtack Guarantee