Some female country artists have a commanding powerhouse voice yet are also gentle and soothing to the ear. Alison MacGregor is one of them and has been budding locally with a country-western sound that hasn’t been represented nearly enough in younger generations.
Alison was raised in a home that was filled with music in a town rumoured to be a nucleus of musical energy: Clavering Ontario. It’s home to musical teacher Betty Ritchie who has helped sprout local musicians like the Ritchie, Williamson and Playford families. Having been raised going to church, she started singing in choir and was a part of the praise and worship team, which is where she carved the structure in her harmonies.
Alison says “when you spend enough time with a choir, your harmonies come into shape reeeeeaally quick”. Her three older siblings had their own musical journeys; her brothers with their own punk band and sister who performed in theatre and school bands. The family shared a passion for musical performance and fully immersed themselves in all their musical endeavours. Her four walls were brimming with harmonies and family jam sessions. It is no surprise she followed the musical route herself.
Today, Alison performs alongside of many well-renowned artists in the area, including JD Crosstown, Matt Epp, and Jesse Corrigan. But, closest to her heart is her longest partner in music: her dad, Scott MacGregor.

Scott has played music as long as he can remember, having a keen ear for bass and vocals. Alison says that “Music is an extension of him, he just wouldn’t be himself if he couldn’t play music”.
Alfie Fromager, Southern Ontario musical icon and previous owner of Fromager’s Music, was a good friend to Scott as they played music together starting in their twenties. Alison describes this time of her dad’s life as one of the most fundamental, as he learned what it took to be a performer and not just a good musician. Her dad’s famous words are “you can be good with music but you gotta know how to be good with people.”
Alison and her father created the MacGregor Two, a classic country duo with a little bit of a twist. Alison has the personality of Mini Pearl according to her dad, a little “corny country humour”. Their act is much like the old Hee Haw television variety show from the 70’s through until the 90’s. The show focused on country music and rural-inspired humour, which has become the premises of the Macgregor Two’s act.

Alison and her dad have always shared a close relationship with no shortage of banter to go around. When the pandemic hit, the family was all back together making music in one household. The livelihood and joy which derived from their time together was too much to be contained; so, the duo decided that people could use a laugh and some classic country tunes in such a dreary time. They began posting videos recorded from their basement and sharing them among friends and family, who couldn’t get enough. The videos were organic and natural between the pair, yet they were never rehearsed. Through the Macgregor Two, Alison and Scott created a fun environment, where they could really lean into hamming it up for the sake of a laugh.
At the close of Covid, the duo had already been connected to the Two Chick’s Café in Sauble Beach, where they were booked for several weekend shows; it is now tradition for this duo to perform where it all began for them each year. As the folks of Grey and Bruce counties have longed for a sound like the MacGregor Two, they have landed several local shows and events, including some of their favourites: the Salmon Spectacular, two successful shows at Heartwood, playing with Dale Revard- a pedal steel guitar legend, and headlined with the Canadian Country Music Hall of famer Larry Mercy.
Alison said her dad even made friends with Lena Welsh, the widow of Stomping Tom, who invited them to perform at her local legion. They’ve recently performed alongside Al Widmyer, a member of the Stompin’ Tom band, and once with five-time CCMA guitar player of the year Steve Piticco. They also held their 2nd Annual Classic Country Christmas Show at the Harmony Centre.

As she continued to perform alongside her dad, Alison later crossed paths with JD Crosstown, who then introduced her to Matt Epp and Jesse Corrigan. The pieces all fell together naturally as she began performing together with the guys, with Alison being the missing ingredient to a few seasoned musicians.
Alison continues to feel refreshed being surrounded by so many incredible musicians, who have encouraged, inspired, and even motivated her along the way. She feels lucky enough to have joined Crosstown and Epp on tour to Germany, broadening her music to greater audiences; she can now say she successfully played in 21 shows over 25 days with these fellas, wow! Alison shared that it’s a little more fun when she gets to let her hair down and just add a little sweetener to their show. She says that she might be selfish while playing with the guys, as she is privileged to be both a part of the audience, and part of the show.

Alison has continued to challenge herself by writing more as a solo artist and wants to build that muscle as she prioritizes her own music. She is grateful to have performed her first original song while on tour in Germany, with the working title If the Heart Knows Where to Go.
MacGregor is a die-hard Emmylou Harris fan; I mean how can you not be with such an astounding force and unmatched tones and phrases. She also enjoys Loretta Lynn’s way of storytelling through her music. With such dominant female musicians paving the way, Alison has echoed their passion in writing her own music. She longs for her music to provide an emotional experience, not just a sound – much like her predecessors. She says, “When I sing, I want to take a person somewhere they’ve been that’s familiar; or maybe somewhere different as a break from reality”.
In 2023, Alison was awarded the prestigious Marie Bottrell Female Entertainer of the Year and the MacGregor Two received the Duo of the Year award. Aside from her music Alison studied at George Brown College for jewelry design; among several commissions, she was granted official permission to craft genuine Wiarton Willie jewelry and gift items.
Alison’s favourite part of performing in the MacGregor Two is seeing people’s excitement to hear old country music, from both the young and old. Providing that kind of joy is rightfully unrivalled in the MacGregor’s household. Having grown up with music, Alison intends to grow old with it too, much like her dad and the many other musicians she has been lucky enough to have been in company with.
She says there is much for her to learn from the many talented folks in her life, and there is nothing quite as healing as a good ol’ belly laugh. This woman has already become a beacon to carry on old time music and classic sounds as the generations age on… man, her Pa must be so proud.
If you’re looking for the next show near you, you can find their coming events on their website https://macgregortwo.ca or on their social media, @themacgregortwo
Written by Ashley Winters
Photos by Ashley Winters and Jem Bautista