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Woodstock has it all, from simple pleasures to extravagant impulses

Dominic Labate and Genia Wickwire by Dominic Labate and Genia Wickwire
November 30, 2025
in Community, Entertainment
0
Santa arrives on the Green in Woodstock on Christmas Eve. (Photos by Dion Ogust)

There is a lively debate (albeit a slightly uninformed misconception) that the town of Woodstock should be characterized as purely and unambiguously, expensive.  While fully aware that Woodstock does maintain its share of particularly posh boutiques, lavish higher-end art dealers and costly hand-crafted jewelry,  Woodstock also presents a myriad of choices for those without singularly deep pockets. Woodstock has literally dozens of stores that encompass a full gamut of prices from the absolutely affordable, the moderate middle and the aforementioned, expensive and borderline exorbitant. Simply put, with an open mind and an only slightly more open pocket, one really can discover something for every person within any price range. 

So, let’s then discuss just a few of the specific attributes we personally love about seasonal shopping in Woodstock. Woodstock has plenty of space to meander and is a harmonious blend of natural and commercial pursuits. If one were to engage in a casual winter walkabout, beginning at the Comeau Property and proceeding directly down to Tinker Street, take a left and head towards The Gilded Carriage. While it may feel as though it lies beyond the main shopping area, there are several hidden gems and stops off-the-beaten-path that are certainly worth checking out before one turns around, takes a chilly deep breath and dives directly into the busiest bit. There are carefully curated bookstores, artist-designed jewelry shops, festive foodie items, silly socks, leather-bound wallets, comfy scarves, stylish hats, locally made art pieces, distinct and flavorful chocolates, beautifully blown glass, handy tools, decorative dishes, fine spirits and colorful t-shirts galore. A well-conceived detour into Houst’s Hardware for your more practically-minded family members will most certainly yield a bounty of useful gadgets, home and hearth items and a range of gifts that once discovered, cannot be ignored. 

Go and discover all that Woodstock has to offer with an open-mind and you most certainly will find the perfect small (or large) gift for anyone in your life. With several delectable restaurants lining your path, you can also stop for a well earned food break. Once again, the choices for a delightful meal range from pizza and meatballs sandwiches to an array of vegan delights to a higher-end, multi-course feast.

Unique feature

Feel free to leave some of your holiday shopping till the last minute as Woodstock is well-known for their Christmas Eve Celebration and the much anticipated arrival of Santa. Until the reveal on that most holy night, no one quite knows the secret of how Santa will arrive. The entire town gathers to witness the festive arrival with shining lights, candy delights and the good-natured crowd.  Stores remain open for any of the gifts one might have forgotten or those which proved to elude even our best attempts at thoughtful gift-giving.

Holiday Open House

Friday, December 5th from 4 to 8 pm. The holiday tree will be illuminated and a merry mood will fill the air above and the streets below.

Parking

Let’s dispel the idea that there is no available or convenient parking in Woodstock. In reality, there are several well-located parking lots that just may, in fact, have space. These parking lots allow one to park just outside the chaos of the center of town so that one can head gradually into town while mentally preparing for the busy center.  Parking is available directly across from The Colony on Rock City Road and while it can be busy, a spot (or two) will often be available. Additionally, one can find ample parking on Comeau Drive. Here is a timely holiday secret: if the  bottom lot is full, the top lot is often empty.  It is a lovely stroll into town from there. Enjoy the season and embrace the giving…it comes but once a year.

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Dominic Labate and Genia Wickwire

Dominic Labate and Genia Wickwire

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