Roam Around Tours conducts walking tours of Janesville’s historic downtown and neighborhoods. Roaming Rich presents the story of Janesville and Rock County through its architecture, history and personalities. The walking tours allow you to experience Janesville on an intimate level by looking at the details and taking the time to appreciate the architecture and place it in historical context. Roaming Rich has over 20 years of guiding experience and has studied and explored history and architecture for over 30 years.

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 A Vintage Holiday in Janesville,  December 16, 2023 2-4 PM
Dec
16

A Vintage Holiday in Janesville, December 16, 2023 2-4 PM

Join Roaming Rich on a nostalgia based Celebrations of Christmases Past in Janesville. This event will take us back in time to when Downtown Janesville was the shopping destination for Christmas gifts from the 1800’s until the 1970s when the Janesville Mall opened. We will revisit the stores that populated downtown and relive the magic of a mid 20th century Christmas. We will also learn about the influence of Charles Dickens on the way we celebrate Christmas and find that some things never change. Enjoy hot cocoa and decorate your own cookies. There will even be a visitor from the North Pole! Join in for some holiday fun as we reminisce on memory lane!

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Once Upon A Midnight Dreary... A  Walking Tour of Gothic Tales, Local Hauntings and Victorian Traditions October 27-28, 2023 7PM
Oct
27
to Oct 28

Once Upon A Midnight Dreary... A Walking Tour of Gothic Tales, Local Hauntings and Victorian Traditions October 27-28, 2023 7PM

Roam Around Tours invites you on an All Hallow’s Eve tour telling gothic tales and victorian traditions. Join guest guide Sir Richard of Roamingwood Manor as you investigate the streets of Janesville under thel moon during the most dreadful season of Halloween. Hear voices of the past, see things that are no longer there and find out what goes bump in the night!

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Boos & Booze: A Halloween Storytelling and Nostalgia Event at Genisa, October 25 5:30 PM
Oct
25

Boos & Booze: A Halloween Storytelling and Nostalgia Event at Genisa, October 25 5:30 PM

Join Roaming Rich for an evening of storytelling under the stars with tales of ghosts, murder and a bit of Halloween nostalgia. Your first drink and a selection of great food from Genisa’s will be included as we roam through local tales, Halloween lore and a bit of nostalgia from the 70’s and 80s.

THIS EVENT WILL BE HELD OUTDOORS ON THE GENISA PATIO BY THE ROCK RIVER. THERE WILL BE HEATERS IF NEEDED. THIS EVENT WILL BE MOVED INDOORS IN THE CASE OF INCLEMENT WEATHER.

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$10 Milton Tour Series - Milton College Neighborhood September 30, 2023
Sep
30

$10 Milton Tour Series - Milton College Neighborhood September 30, 2023

Join Roam Around Tours in partnership with the Milton Historic Commission for a summer series of Milton History Tours. Milton College and its predecessor, Milton Academy was an integral part of Milton until its closure in the early 1980s. The buildings that made up the college campus have remained and serve as a historic legacy was a respected small institution that hosted students from all over the US and the world.

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Autumn Stroll of Courthouse Hill September 23, 2023 10 AM
Sep
23

Autumn Stroll of Courthouse Hill September 23, 2023 10 AM

Join Roaming Rich on an Autumn Stroll of Courthouse Hill. Courthouse Hill has always been a special place to live and the fall gives us a good time to enjoy this great collection of Victorian homes. On this one hour tour, we will explore Janesville architecture and history from the early settlers to the home of a recent Speaker of the House of Representatives. As a thank you, we will stop and have a treat and drink among the beautiful fall atmosphere and architecture.

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Tales of Spirits, Murder and Peril in Downtown Janesville Friday, September 15, 2023
Sep
15

Tales of Spirits, Murder and Peril in Downtown Janesville Friday, September 15, 2023

Join Roaming Rich on a tour of the darker side of Janesville. We will explore what haunts Downtown Janesville and Rock County, murders and stories of tragedy and peril from the 1800s. This one hour tour will leave from The Marv Pavilion on Main Street at 7PM on September 15, 2023! It will be a great way to kick off the “Spooky Season”. Tour cost is $20.

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Art, Adventure & Wheels: A Free Art Infusion Scooter Tour of Downtown Janesville September 9, 2023
Sep
9

Art, Adventure & Wheels: A Free Art Infusion Scooter Tour of Downtown Janesville September 9, 2023

  • Janesville Area Convention and Visitors Bureau (map)
  • Google Calendar ICS

Join Roaming Rich and Janesville Art Infusion for a free and art filled scooter tour through Downtown Janesville! We will view the many murals throughout Downtown and stop and see the new art being created during Art Infusion. Only 8 spots available per 40 minute tour. Pre Registration is required for one of the three tours offered: 11 AM, 2PM and 4PM. The scooter will be provided. YOU MUST BE 18 to ride and you must sign a waiver from the scooter company. The wearing of a helmet is highly suggested.

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Milton Tour Series: Goodrich Park, The Milton House and the Beginning of Milton
Aug
19

Milton Tour Series: Goodrich Park, The Milton House and the Beginning of Milton

Join Roam Around Tours in partnership with the Milton Historic Commission for a summer series of Milton History Tours. Goodrich Park and The Milton House mark the true beginnings of Milton. This one hour tour will explore the beginnings of Milton and highlight the unique grout buildings and show the growth of Milton.

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Walking Tour of the Old Fourth Ward Historic District August 12, 2023 10 AM
Aug
12

Walking Tour of the Old Fourth Ward Historic District August 12, 2023 10 AM

Join Roaming Rich for a great walking tour of the Old Fourth Ward Historic District. We will meet at St. Patrick’s Church and venture through one of Janesville's oldest and most diverse neighborhoods. This neighborhood is rough around the edges, yet it contains some true architectural gems and also the immigrant story told through its remaining church buildings.

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A Midsummer Night's Scream Janesville Ghost Tour July 28, 2023 8 PM
Jul
28

A Midsummer Night's Scream Janesville Ghost Tour July 28, 2023 8 PM

Let’s explore the darker side of Janesville! From true crime, hauntings, local lore and legends, Janesville is full of “life” after dark. This one hour tour takes us on a journey to the other side of Janesville. Join us if you dare!

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 Milton Tour Series - Milton Junction July 20, 2023 6PM
Jul
20

Milton Tour Series - Milton Junction July 20, 2023 6PM

Join Roam Around Tours in partnership with the Milton Historic Commission for a summer series of Milton History Tours. Milton Junction grew as a railroad transportation hub in the 1850s. This one hour tour will explore “Merchant Row” and the surrounding neighborhood of businesses and grand victorian homes. Less than a mile from Milton, the two towns developed independently, but their proximity made their history intertwine until ultimately merging in the 1960s.

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Walking Tour of the Courthouse Hill Historic District in Janesville July 8, 2023 10 AM
Jul
8

Walking Tour of the Courthouse Hill Historic District in Janesville July 8, 2023 10 AM

Join Roaming Rich on a walking tour of the Courthouse Hill Historic District. High on a bluff on the east side of the Rock River, Courthouse Hill has always been a desirable place to live. Homes dating from the 1850's to the 1930's gives you a diversity of grand architecture. You will learn about the Victorian architecture and the people who have made this part of Janesville home.

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Ice Cream Walk of Downtown Janesville.   Thursday July 6, 2023.  6PM
Jul
6

Ice Cream Walk of Downtown Janesville. Thursday July 6, 2023. 6PM

Grab an ice cream cone from the Sugar Exchange and we will meet out back to take a one hour evening stroll around downtown. We will explore the history, but also some of the businesses that were located along the Rock River, including a popular Janesville dairy! Let’s take a step back in time, on a warm summer evening and let the memories lead our way.

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Springtime Stroll of Downtown Janesville April 29, 2023 at 10 AM
Apr
29

Springtime Stroll of Downtown Janesville April 29, 2023 at 10 AM

Join Roaming Rich on April 29 at 10 AM at the Heritage Bridge at Town Square in Downtown Janesville. We will explore Downtown Janesville and discover the history and architecture that makes our community special. New murals and new development is continuing the evolving history of our hometown. Let’s stretch out legs after the long winter.

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The Irish in Janesville History Walking Tour
Mar
18

The Irish in Janesville History Walking Tour

Join Roaming Rich of Roam Around Tours as we celebrate St. Patrick’s Day on a one hour tour that takes you to Ireland and Janesville! We will explore through the mists of time to bring Irish legend, lore and the story of Irish immigration to Janesville and Wisconsin.

Tour starts at Noon on March 18, 2023 and be prepared for some Leprechaun magic to help lead the way.

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Boos and Booze: An Evening of Halloween Storytelling and Nostalgia at Genisa October 26, 2022 5:30 PM
Oct
26

Boos and Booze: An Evening of Halloween Storytelling and Nostalgia at Genisa October 26, 2022 5:30 PM

Join Roaming Rich for an evening of storytelling with tales of ghosts, murder and a bit of Halloween nostalgia. Do you remember dressing in your costume with a plastic mask that came in a box? Did you walk quickly past that big old house that everyone said was haunted? Remember the anticipation of all that candy you would get from Trick or Treat….come out and share with Roaming Rich tales of Halloween past and who may, or may not still haunt the streets of Janesville. Your first drink and a selection of great food from Genisa’s wood fired ovens will be included as we roam through local tales, Halloween lore and a bit of nostalgia from the 70’s and 80s.

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Walking Tour of the Old Fourth Ward Historic District October 1, 2022 10 AM
Oct
1

Walking Tour of the Old Fourth Ward Historic District October 1, 2022 10 AM

Join Roaming Rich for a great walking tour of the Old Fourth Ward Historic District. We will meet at St. Patrick’s Church and venture through one of Janesville's oldest and most diverse neighborhoods. This neighborhood is rough around the edges, yet it contains some true architectural gems and also the immigrant story told through its remaining church buildings.

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Walking Tour of Downtown Janesville September 8, 2022 6 PM
Sep
8

Walking Tour of Downtown Janesville September 8, 2022 6 PM

  • Town Square - Blain Gilbertson Family Heritage Bridge (map)
  • Google Calendar ICS

Join Roaming Rich for a tour of Janesville’s historic and dynamic downtown. This evening tour takes us on a time travel journey from the 1830’s to today. The beautiful victorian buildings, the hidden secrets and the vibrant new mural art work will all be featured on the one hour tour.

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FREE Milton Tour Series - Milton Junction September 7, 2022 6PM
Sep
7

FREE Milton Tour Series - Milton Junction September 7, 2022 6PM

Join Roam Around Tours in partnership with the Milton Historic Commission for a summer series of Milton History Tours. Milton Junction grew as a railroad transportation hub in the 1850s. This one hour tour will explore “Merchant Row” and the surrounding neighborhood of businesses and grand victorian homes. Less than a mile from Milton, the two towns developed independently, but their proximity made their history intertwine until ultimately merging in the 1960s.

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Walking Tour of the Prospect Hill Historic District August 13,2022
Aug
13

Walking Tour of the Prospect Hill Historic District August 13,2022

Join Roaming Rich, of Roam Around Tours, for a one hour walking tour of the Prospect Hill Historic District in Janesville. Meet at 10 AM in front of St. Mary’s Catholic Church on one of the highest points in Janesville. We will take a step back in time and see the Victorian homes that show off on the streets adjacent to Court House Park.

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Walking Tour of the Courthouse Hill Historic District in Janesville August 11, 2022
Aug
11

Walking Tour of the Courthouse Hill Historic District in Janesville August 11, 2022

Join Roaming Rich on a walking tour of the Courthouse Hill Historic District. High on a bluff on the east side of the Rock River, Courthouse Hill has always been a desirable place to live. Homes dating from the 1850's to the 1930's gives you a diversity of grand architecture. You will learn about the Victorian architecture and the people who have made this part of Janesville home.

View Event →
Milton Tour Series - Milton College Neighborhood
Aug
10

Milton Tour Series - Milton College Neighborhood

Join Roam Around Tours in partnership with the Milton Historic Commission for a summer series of Milton History Tours. Milton College and its predecessor, Milton Academy was an integral part of Milton until its closure in the early 1980s. The buildings that made up the college campus have remained and serve as a historic legacy was a respected small institution that hosted students from all over the US and the world.

View Event →
Milton Tour Series: Goodrich Park, The Milton House and the Beginning of Milton
Jul
16

Milton Tour Series: Goodrich Park, The Milton House and the Beginning of Milton

Join Roam Around Tours in partnership with the Milton Historic Commission for a summer series of Milton History Tours. Goodrich Park and The Milton House mark the true beginnings of Milton. This one hour tour will explore the beginnings of Milton and highlight the unique grout buildings and show the growth of Milton.

View Event →
Walking Tour of the Courthouse Hill Historic District in Janesville
May
14

Walking Tour of the Courthouse Hill Historic District in Janesville

Join Roaming Rich on a walking tour of the Courthouse Hill Historic District. High on a bluff on the east side of the Rock River, Courthouse Hill has always been a desirable place to live. Homes dating from the 1850's to the 1930's gives you a diversity of grand architecture. You will learn about the Victorian architecture and the people who have made this part of Janesville home.

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Lucky Leprechaun -Irish History Tour of Janesville!
Mar
12

Lucky Leprechaun -Irish History Tour of Janesville!

Join Roaming Rich of Roam Around Tours on a one hour tour that takes you to Ireland and Janesville! We will explore through the mists of time to bring Irish legend, lore and the story of Irish immigration to Janesville and Wisconsin.

Tour starts at Noon on March 13, 2021and be prepared for some Leprechaun magic to help lead the way.

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