4 Must Do’s For Holiday Shopping to Ignite Your Spirit & Nourish Your Community

There are two kinds of people in the world–those who eagerly anticipate Black Friday, and those who do not. 

For those who would rather meander, chat, and sip cider during their holiday shopping, here are four steps to ensure that your holiday shopping is appreciated by you, your gift recipients, and your community.

1) Always write a list the night before.

My holiday shopping began this weekend, or at least that was my plan when I arrived at the Campwoods Holiday Craft Fair, the first local event of its kind for the season. I ended up buying myself a new jacket and earrings, then ordering my Christmas wreath from the Girl Scouts to be delivered in a few weeks. 

Obviously, I know some of the people I plan to purchase gifts for, but since I hadn’t dedicated time to thinking about each friend or loved one that I want to shop for this year, the only potential gift recipient’s desires I could easily call to mind was… me. Next weekend, to prevent this pitfall, and foster the spirit of giving, I will write a list of recipient names and gift ideas inspired by what they’re experiencing in their lives right now, what gifts they’ve appreciated in the past, what they enjoy doing, or simply their favorite color. 

So, my first $98 dollars of holiday spending has brought me no closer to accomplishing my goal of finishing my holiday shopping by mid December. If you add the empanada I purchased from the food truck on my way out, I passed the $100 threshold on Day 1. And more importantly, my shopping experience lacked the sense of holiday spirit that comes from the satisfaction of discovering a delightful gift that you know will be appreciated.

2) Predetermine a price range.

Saturday was a beautiful November afternoon that invited lingering at booths outdoors and in the unheated church sanctuary/auditorium that hosts this annual holiday fair. With so many creative and colorful items, it’s hard to focus on thoughtful ideas for particular people. 

One practical way to prevent overwhelming distraction in a room full of shiny, colorful items, is to come up with a range of how much you plan to spend on each person. Depending on your disposable income this season, this step might be critical to avoiding going into debt for the holidays. But regardless of your current financial situation, from a practical perspective, this is a good way to work backwards by focusing on items at a particular price point and identifying if they may be a good match for someone on your list.

3) Shop small & invest big.

Every dollar you spend in a nearby small business or directly to a local maker, is an investment in your community and an act of environmentalism. My husband owns a local brewery, and I know how much he appreciates customers who like his business so much that they want to share it with friends with a gift card, product, or merchandise. If minimizing your environmental impact at every opportunity matters to you, shopping local is often a good way to identify businesses that have a short supply chain from grower, to manufacturer, to seller. 

When you shop local, your dollar has a short path to reinvestment in the community. Every dollar that pays the wages of a local worker or maker is likely to be spent in the very near future, quite possibly at another local business. Here’s one of many studies that quantifies the value of shopping small.

4) Mark your calendar for shopping as social events.

Whether you go on a shopping date with a friend or are just wandering through your downtown, holiday shopping can and should be a social occasion. The best way to foster this kind of shopping experience is to avoid Black Friday Extravaganzas and last minute scrambling. I have friends who love Black Friday shopping, and for them it’s a beloved family tradition. I have no such nostalgic connection to that day of violent consumerism. 

When I left the holiday market on Saturday, even without making any progress on my so-far theoretical list, I did so with a buoyed spirit. I engaged in conversations with artisans I met for the first time, fellow moms raising funds for youth-oriented community organizations, veteran vendors I’ve shopped with for years, and I found a new seamstress with a side gig indulging her passion for upcycling tweed.

Taking this socially indulgent approach to shopping also makes it less likely that you’ll find yourself purchasing overpriced, under-appreciated last minute gifts on Christmas Eve.

Chances are your community has holiday festivals scheduled for most of November and December. Small Business Saturday has become a national event, amplified by American Express, and practiced through local communities across the nation. Below is a list of events I have added to my calendar so far. If you live in the Ossining area, maybe I’ll see you. This is certainly not an exhaustive list, so please tell me what more to add!

Campwoods Holiday Craft Fair: November 11, 11AM-4PM (TODAY)

This is where my holiday shopping began. It’s very community focused and always a friendly environment. Click here for details.

Ossining Small Business Saturday Scavenger Hunt: November 15-29

The event actually spans two weeks around Small Business Saturday as shoppers are invited to pick up a scavenger hunt card at any participating Ossining business, collect stamps around town as they shop, and enter their card to win prizes from local Ossining businesses. To amplify the local holiday gift opportunities, participants are encouraged to share pictures of their shopping experience using the hashtag #ossiningsmallbizsat22. Participating businesses include: Beasley’s Lock Shop, Brothers Fish and Chips, D’Martins Barber Shop, Fable Farm, First Village Coffee, Hudson Valley Books for Humanity, Laura-Lee Sports, Lina Londono Hair Salon, Melita’s Home, MF Jewelers, Mike Risko Music, Nova 21 Beauty Supply, Penny & Ting, Quimbaya Picante, Shine Salon & Spa, Sing Sing Kill Brewery, The Boathouse, Tasty Table, Theater O, Westchester Cell Phone & Computer Repair, Woods Bar & Grill

Ossining Arts Council’s First Annual Small Works Holiday Show: Saturdays November 19 thru December 24 + Reception on Friday, December 2

117 Main Street, Ossining (upstairs)

Local artists are selling small pieces for one uniform price on Saturdays, plus they’ll be participating in Ossining’s First Friday the evening of December 2 when lots of local establishments hold events encouraging a festive atmosphere for shoppers and revelers.

Magical Holiday Pop-up Market at Melita’s: November 26 & 27

125 Main Street, Ossining

If you aren’t already familiar with Melita’s in downtown Ossining, you’re missing out. On Shop Small weekend, Melita invites local artisans to sell their creations in the hallway adjacent to her shop. (Melita is a beloved powerhouse in local business and owns the whole building). 

Holiday Boutique at Philipsburg Manor: December 2-18, Friday-Sunday

381 N. Broadway, Sleepy Hollow

Beyond the chance to shop at the Holiday Boutique, every weekend also includes a special activity somewhere on the Restoration property. These events sometimes require tickets ranging in price from $0-$5. I’ve already gotten tickets for my mom and I to attend the Holiday Tea Party in the Philipsburg Manor Greenhouse on December 17. Other events included a S’mores Bar, Cocoa Under the Stars, Gingerbread Cookie Decorating, and a Meet and Greet with the barn cat Ginger. Click here for tickets.


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