When: Dec. 4, 2021

Time: 10:00am - 3:30pm*

Where: Hopkinton Chamber Businesses

Passport: Print here

Facebook Event Page

It's Holiday time again! Let's celebrate at our 2021 Hopkinton Chamber of Commerce Holiday Stroll. It will be a great way to get all of your shopping done, get a chance to win a $300.00 cash prize and have a fantastic time doing it! Go from store to store by foot or cover much more mileage by taking your own vehicle. 

Many of our Chamber businesses will be participating with sales, specials, contests, treats and promotions to make your holiday shopping easy and fun. We can't wait to share all of the days events here with you! "Like" our Holiday Stroll Events page to be kept up-to-date on Holiday Stroll Announcements!


Photo Gallery Last Holiday Stroll

This community event in Hopkinton  encourages people to visit Chamber Businesses and shop local, gather for festivities and celebrate together as a community. It is a well-attended event and will culminate with the Girl Scouts of Hopkinton's annual lighting of the tree on the Town Common that evening. Girl Scout's Activities.

HOW to enter for your chance to win:

  1. Visit a total of 24 participating Chamber business locations and have your Holiday Stroll Passport stamped with each business’s unique stamp for a chance to win a $300 cash prize! (Multiple cash prizes to be awarded)

  2. Must have a minimum of 6 businesses stamped in each of the 4 quadrants. 

  3. Use your phone to take a picture of your stamped passport with legible contact info, and Email the picture by 2:00pm, Dec. 5th, 2021 to: info@hopchamber.com to be entered into a random drawing for $300 cash prize!

Passports and Guides available at the participating businesses leading up to the Stroll on Dec. 4th or download here or get your Nov. 24th Edition of the Hopkinton Independent for the Passport Insert.

Be sure to "Like" our Holiday Stroll Events page to be kept updated!


And new this year is a complimentary Horse Drawn Carriage ride around the Hopkinton Common! 1:00pm to 3:30pm

Chance to win $300.00 cash prize!

Holiday Stroll 2021

This year's Holiday Stroll is Dec. 4, 2021.  Don't miss it!
Event Sponsored by:
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Holiday Stroll 2021 Participating Businesses!

Baystate Audiology:  Holiday themed activity!

Bill's Pizzeria:  Special Holiday Pizza Slices - A Holiday Punch for Adults.

Burns Law Office, P.C.:  Individually wrapped holiday gift bags with holiday cookies and festive holiday music.

Cabinet Gallery:  We will be providing raffles, reindeer games, coffee refreshments, crafts for kids and will have shopping available featuring our subsidiary company Cabby Chic Up-cycled Cabinetry.

Cedar Chiropractic & Sports:  Join us as we take part in the annual Hopkinton Holiday Stroll event on December 4th, 2021! To make the holiday brighter, we are working with Project Just Because to collect new unwrapped toys or board games. Feel free to drop them off at our location during your visit. Anyone who brings in a donation on that day will be entered into a raffle drawing. We’ll provide food, drink and fun activities to ring in the holiday season.
*Central Public House (Opens at 4:00pm. Stamping available until 6:00pm):  Stop in to win a gift card as well as get your passport stamped! Stay afterwards for our delicious apps, entrees and desserts!

Charlesbank Realty Group:  Not open that day but supporting all the Businesses who are part of the Stroll!

Christine Strickland Photography:  Holiday themed activity! 2nd Floor of the Hopkinton Center for the Arts.

Edward Jones Financial Advisor:  Hot Chocolate and a Kids Craft.

Gorman Richardson Lewis Architects:  Give aways! Free notepads & binders!

Guaranteed Rate:  Candy cane scavenger hunt.
Hiller's Pizzeria:  Holiday themed activity!

Hopkinton Center for the Arts:  Festival of wreaths in the gallery. They are all unique wreaths designed by artists and community members and will be available to bid on and take home for the holidays!
Hopkinton Drug:  Raffle baskets, coupons, a warm drink station, popcorn and special treats for our customers!

Hop-Yo:  Stop by Hop-yo for some delicious Fro-yo, warm fresh soup, Hot-Cocoa Bombs as well as a raffle, holiday arts and crafts and local gifts to shop.

Little Brown Barn Boutique:  Holiday themed activity! 2nd Floor of the Hopkinton Center for the Arts.

M. Jackson Accounting:  Holiday treats for adults and kids!

Main Street Pediatrics:  Raffling off some gifts baskets and gift cards at the holiday stroll!

MetroWest YMCA:  Giant Connect 4 and Jenga games along with information on the new regional YMCA.! 2nd Floor of the Hopkinton Center for the Arts.

MyFM 101.3:  Meet the MyFM 101.3FM Street Team at Weston Nurseries, getting your passbook stamped and enter to win some festive prizes they will be hosting.

Oasis Wealth Advisors:  Popcorn machine and we will play a holiday mini golf challenge and will have goodie bags with our info as well as candies and toys!

Platinum Physical Therapy, Inc.:  A holiday fitness challenge with prizes at our location!

Ostrander Insurance:  For Kids: Guess the amount of candy in the jar, Closest to the correct amount wins $50 VISA gift card! Adults: Guess the amount of candy in the jar, Closest to the correct amount wins $50 gift card to Start Line Brewing Co.! And Ballons for all!!
Resilience Fitness:  Children friendly (indoor) yard games, a camping-themed winter wonderland of blow-up North Pole characters, including a Letter-to-Santa station, for entertainment. And Holiday themed snacks for all.
Shahood & Sons, Inc.:  Holiday themed activity!

Start Line Brewing Company:  Start Line Brewing will be a fun stop during the Hopkinton Holiday Stroll. Start Line will open at 11:00am and will be releasing Hop Load Holiday IPA, a special seasonal Hazy IPA. Enjoy live music by the Bill Fanning Quartet and our traditional fun, food and beverage during your Stroll!

Swoon Central:  Swoon will do a photo booth. Participants can take photo and tag Swoon on Instagram and/or social media to be entered into a drawing for $100 gift card.

The Vin Bin:  Homemade mulled wine to taste, as well as kits to purchase to make it at home!

Unibank:  Holiday themed activity!

Webster First FCU - (Open 10:00am-1:00pm):  Lip balm, Hand Sanitizer, Mood pencils, Sun glasses, Kids coloring books. In addition we will be raffling off a gift basket (valued at $50.00). We will be open to visitors from 10-1. Masks are required to enter!

Weston Nurseries Garden Center:  Weston Nurseries will have all the holiday spirit this year…join us for great food from some of our most popular food trucks, MYFM101.3 will be playing holiday music, we will have carolers, special gift vendors, and of course there will be giveaways, prizes and surprises all day long! Come get your Christmas trees and wreaths, swag, ornaments, holiday snow globes, poinsettias, paperwhites, and gifts for everyone on your list this year! We have everything you need to make your Christmas merry and bright!!
Your College Funding Coach:  Giving away note pads and portfolios! 2nd Floor of the Hopkinton Center for the Arts.