Chester’s thoroughfares are welcoming visitors this holiday season with an exciting mix of merriments sponsored by the Historic Chester Business Association (HCBA).

A variety of eateries and shops—offering delectable treats, imaginative gifts, and treasures—are just waiting to be discovered! Holiday Activities (with individual event dates and times) include:

SC3 Holiday Music / Outdoor DJ Entertainment

Renowned DJ Chris Schmidt of S.C.3. Entertainment will be streaming classic holiday tunes from his “Decked-Out” trailer on Main Street to make the *Season Bright and Festive* while you Shop, Dine & Explore Historic Chester! Spinning the “Sounds of the Season” throughout Chester’s Downtown Main Street on Fri., Nov. 29th & Sat., Dec. 21st from 12:00 noon to 4:00 pm.

Small Business Saturday: November 30th, 2019

Keeping our neighborhood shops in business…that’s what Small Business Saturday is all about! Shop and Dine Historic Chester on Sat. Nov. 30th and support your local HCBA Member businesses throughout the entire holiday season!

Chester Brass Works Quartet Ensemble

Come hear a festive mix of classical and popular holiday music presented by the amazing Chester Brass Works Quartet Ensemble. Strolling throughout Historic Downtown Chester to brighten your holiday shopping and dining experience on Sundays, Dec. 1st, 8th, and 15th from 1:00 pm to 4:00 pm.

Strolling Dickens’ (Manhattan Holiday) Carolers

No holiday celebration is complete without the stunning sights and sounds of Manhattan Holiday’s a cappella caroling quartet! Performing a variety of traditional and contemporary holiday classics in beautiful hand-made Victorian-style costuming, these troubadours will be strolling throughout Downtown Chester on Saturdays, Dec. 7th & 14th from 12:30 pm-4:30 pm.

Santa’s Comin’ to Town!

Jolly Ol’ Saint Nick will be spreading holiday cheer and giving good little boys and girls a chance to join him in some ‘Santa Selfies.’ Meandering merrily throughout Downtown Chester on Sat., Dec. 7th, Sun., Dec. 15th, and Sat., Dec. 21st from 1:30 pm to 3:30 pm.

Sculpted Ice Works

The “cool” ice designs by Pennsylvania’s own Sculpted Ice Works are truly works of art! Using chain saws, chisels, torches and more, come watch one of their talented ice carvers hack away at large blocks of ice to reveal spectacular creations on Sun., Dec. 8th from 12:00 noon to 4:00 pm.

Ron Albanese as ‘Elvis the Elf”

Bring the kids for a great “Selfie” with Santa’s Favorite Singing Elf – ELVIS! Performing throughout Downtown Chester on Sundays, Dec. 15th and 22nd from 1:00 pm to 4:00 pm


Trendy boutiques, distinctive dining and traditional holiday festivities for the whole family. Happy Holidays to All! For a list of all HCBA member businesses and holiday event details, visit