albany park's first sip, shop & trolley hop

sip, shop & trolley hop

If you follow us on Instagram, you know December 14th we were part of Albany Park's first Sip, Shop & Trolley Hop. What you may not realize is this event was spearheaded by yours truly. During the summer, I started finalizing my 4th quarter calendar with shows and events. I noticed a few gaps and thought how amazing would it be if we could host a neighborhood event. After all, there is strength in numbers. In September, I reached out to my building neighbors asking if they'd be interested in hosting a Sip & Shop and maybe a neighborhood Sip, Shop & Stroll. Everyone was on board and I set the dates for November 30th and December 14th.

Like many things in small business, not everything went according to plan. I had planned to reach out to neighborhood businesses in September. Instead, my September was filled with reprinting holiday cards, prepping for holiday shows and ordering products for our retail space. I was working a ton and coming in on Sundays when I could have the print shop to myself. I also have an annual vacation in September, which means I work twice as hard two weeks before and two weeks after to just keep up. It was a lot. October came and I continued printing most days, cutting, scoring and all the other things that go into creating your own products. It was very busy and emails started to slip. A sure sign I'm overextended. I had a message ready to copy and paste and send to neighborhood stores for the Sip, Shop & Stroll, yet it wasn't happening. Instead November 1st came and I paniced and knew it was now or never. We still had six weeks to plan, create and promote the event. My goal was for people to visit all the amazing small boutique shops popping up in Albany Park. The last couple years have brought a diverse group of businesses and sadly, very few people realize this. Chicagoans (me included) have a way of sticking to our block, our commute, our regular routes and walks, rarely venturing out. Unfortunately, that's how we miss a lot of new businesses. I had envisioned all the neighborhood shops open late one Thursday night, serving holiday spirits and patrons strolling from store to store, discover the amazingness Albany Park has for shopping.

 our building

Most of the stores I reached out to, showed interest immediately. Two of those stores, Him + Her Vintage and The Scent Queens Candle Co. & Apothecary Shoppe, offered to help any way they could. Immediately, they had ideas of a traditional, holiday trolley to help get customers to all the shops. Which I loved but thought would be a goal next year, or even the following, simply because, we had no budget. Like none. Our biggest hurdle would be financing a trolley and finding one available that night. After asking for help from our Chamber and Alderwoman, we realized if we wanted a trolley, it was up to us to figure out. Keep in mind, it was already mid-November and our event was only 4 weeks away. There was a lot of pressure to make a trolley decision and fast, if we wanted to promote the event for Small Business Saturday. Two days before Thanksgiving, Curtis from The Scent Queens Candle Co. and Apothecary Shoppe and Andrew from It's Lit Studio, reached out offering to finance the trolley. A very generous and unexpected offer. And also very exciting! We elevated from a stroll to a trolley the first year, actually within the first three weeks. I had ONE day to design all the identity, which is crazy and I can't believe I pulled it off, as well as create the Eventbrite, create a QR code, make a map, design banners for Eventbrite, link all the businesses to the event, design and print postcards and posters, all so we could promote it on Small Business Saturday. It was a sprint! Not gonna lie, it was very stressful and I honestly didn't have the time or energy to dedicate to it while finishing last minute wholesale holiday orders, prepping for Thanksgiving dinner and Small Business Saturday. Mr. Favorite bared the brunt of my family neglect, he's the unsung hero of the entire event, in my opinion, he picked up my slack at home and stepped up to share his marketing game and make sure we did all we could to have a successful event. He took care of the Evenbrite and QR code and focused on social media, things he's much, much better at than me. During this entire time Myriam from Him + Her Vintage and Curtis from The Scent Queens Candle Co. and Apothecary Shoppe and I were dreaming and scheming about the event, messaging each other daily and forming a very fun friendship. It's been the highlight of the entire event for me.


Everything was set for our first Albany Park Sip, Shop & Trolley Hop. We overcame a lot of hurdles along the six short weeks we had to plan and truthfully, we couldn't plan much until we knew if the trolley was a go or not. That brought our planning down to three weeks total, half of what I thought we had, no easy feat. However, the three of us - Myriam, Curtis and I, with the help of our spouses, made it all happen. By the time December 14th rolled around, we were ready!

Manny Clause & me

To elevate our event even more, Myriam invested in a beautiful Santa costume and enlisted the help of her husband, Manny to play Santa Claus. When I tell you Manny created magic the entire evening, I'm not exaggerating. He stepped up and rode the trolley the entire evening, leading riders in song, letting kids sit with him and listening to all their hopes and dreams and be as jolly as the real Santa all night long. He was the best Manny Claus EVER. He truly made the night special. When the trolley rolled up at 4pm, I was so excited. It was a classic Chicago trolley with lighted garland and a wreath. It was perfect. When our Manny Claus climbed aboard, I couldn't help but yell "SANTA IS HERE!" like a child. It was magical. The night was long but also crazy, fun. The neighborhood really loved it. We heard all night long what a fun event it was and also how people had no idea so many amazing businesses are in the neighborhood. Which to me, means it was a success.

santa shopping local

We learned a lot along the way and have notes and many ideas to make next year even better. Thanks to everyone who shared our posts, donated, came out that night and shopped our businesses. We appreciate you! Thanks to all the businesses who participated - 51st Ward Books, Artesanias La Luna, Anchor Baby Vintage, Cafe Urbano, Gemz and Boardz, Green Spaces Plant Shop, Gypsy Alley, Him + Her Vintage, It’s Lit Studio, Katherine Anne ConfectionsMake it Happen, Manual, Miel y Canela, Northside Kung FuSincerely Herrera, The Chi-est Beauty, The Chi-est Part of Town, The Scent Queens Candle Co. & Apothecary Shoppe

A HUGE thank you to my partners in planning and new friends - Myriam and Curtis, I am always willing to collaborate with you two, thanks for stepping up and elevating us all. Everyone, please save the date for next year's event - Thursday, December 12th, 2024.

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