Blog ArchiveDowntown Pittsfield Passport 2023

Downtown Pittsfield, Inc. (DPI) will be facilitating a Holiday Downtown Pittsfield Passport giving shoppers a chance to win one of three prize packages made up of donations from the 40 participating local businesses. The grand prize value will be over $500. The promotion will run Friday, November 24 through Sunday, December 3 and will encompass Black Friday, Small Business Saturday, and DPI’s Festive Frolic (December 1-3).


A person can collect one sticker from every business/location where they make a purchase* or attend an event (free or not), and the more stickers they collect, the greater their chance of winning the Downtown Pittsfield Prize Package. 46 stickers are available. Each sticker equals one entry to win the prize packages.


The Downtown Pittsfield Passport will be available at participating businesses and locations starting Friday, November 24. (Event locations may only have them available during their event.)


Completed Passports must be turned in to a participating location by Sunday, December 3.


Participating Businesses include:


101 Restaurant & Bar, 1 West Street

Barrington Stage Company, 30 Union Street

Berkshire Fitness and Wellness Center, 137 North Street

Berkshire Museum, 39 South Street

Berkshire Theatre Group, 111 South Street

Berkshire Yoga Dance & Fitness, 55 North Street, Suite 201

Bottomless Bricks, 163 South Street, Suite 4

Budhaus, 239 West Street

Carr Hardware, 547 North Street

Clark Vintage Lighting, 342 North Street

Deidre’s Special Day, 2 South Street

Dory & Ginger, 299 North Street

Elegant Stitches, 237 First Street

Hot Harry’s, 37 North Street

Hot Plate Brewing Co., 1 School Street

Kidding Around Consignment, 700 North Street

LuLu’s Tiny Grocery, 137 North Street

Mana Crypt Gaming Center, 139 West Housatonic Street

Marketplace Cafe, 53 North Street

Methuselah Bar and Lounge, 391 North Street

Miller Supply Company, 205 West Street

Museum Outlets, 31 South Street

Otto’s Kitchen & Comfort, 95 East Street

Patrick’s Pub, 26 Bank Row

Paul Rich & Sons, 242 North Street

Peace Train Tees, 2 South Street

Phoenix Theatres Beacon Cinema, 57 North Street

Plaine’s Bike Ski Snowboard, 55 West Housatonic Street

Schilling TV, 215 Fourth Street

Soma’s Aromas, 81 East Street

Steven Valenti’s Clothing, 157 North Street

The Recovery Room, 32 Bank Row

This & That Sports, 128 Fenn Street

Thistle & Mirth, 46 West Street

Tito’s Mexican Bar & Grill, 34 Depot Street

Witch Slapped, 78 North Street


Bonus Passport Stickers can be obtained by making a purchase at the following locations:

413Shirts, 1595 East Street, Pittsfield

Berkshire Mountain Distillers, 356 South Main Street, Sheffield

Berkshire Roots, 501A Dalton Avenue, Pittsfield

Shaker Mercantile at Hancock Shaker Village, 1843 West Housatonic Street, Pittsfield

Or by paying the entry fee at Roots Rising’s Handmade Holiday Festival on November 25 and 26 at The Stationery Factory


There is also an opportunity to attend downtown events to receive Passport Stickers:

1) Wreath Art Auction to benefit the South Community Food Pantry on Friday, December 1, 5 to 7 pm

2) Pittsfield Farmers Market at the Zion Lutheran Church on Saturday, December 2, 9 am to 1 pm

3) Free Kids’ Paint & Sip at St. Stephen’s Episcopal Church on Saturday, December 2, 12 to 3 pm

4) Photos with Santa at The Beacon Cinema on Saturday, December 2, 12 to 3 pm

5) Festive Frolic Holiday Market featuring a Krampus Beer Garden on Sunday, December 3, 12 to 4 pm