Pop into the shops you love and win! The one-of-a-kind shopping excursion is returning on Small Business Saturday, November 28 🎉

Explore more than 25 Downtown shops and stores while collecting stamps to win thousands of dollars in prizes in this socially-distanced city excursion just in time to kick off your holiday shopping.

New! Pass go at Key Bank to collect Community Chest and Chance cards for instant giveaways. Read more below.

Saturday, November 28
11:00 a.m. – 4:00 p.m.
Downtown Pittsburgh

Safety Guidelines

Stores and stops are spread around the Downtown neighborhood, meaning it’s easy to explore at your own pace.

  • Wear a mask, which is required when walking around Downtown and inside stores and businesses. Read more about Pennsylvania’s Universal Masking requirement.
  • Practice social distancing and maintain 6 feet between yourself and other groups, when possible. If a store is busy, come back to it later.
  • Stores and locations may have reduced capacities, but will be working hard to ensure a safe, pleasant experience. Thank you for your patience!
  • Stay home if you’re not feeling well. Plenty of Downtown’s stores offer online shopping.


Prizes will be awarded by a drawing taking place on Monday, December 7, with the winners contacted the following day. Those eligible for each category will be entered into the random drawing, with each game card eligible for one prize.

Grand Prizes

Collect a stamp from every participating store to be entered to win one of the Grand Prizes listed below.

  • A 14k white gold diamond necklace valued at $2,200 from Brooks Diamonds and Rothschild Trading Company
  • A free one-night-stay at the Hotel Monaco with dinner for two at The Commoner

Additional Prizes

Collect at least one stamp from each color category to be entered to win.

  • $100 gift card to Joseph Orlando Clothiers
  • $100 gift certificate to Altus HPO
  • 1 fully customizable private Clean Yoga experience at Aither Yoga
  • Coffee bundle from Rock ‘n’ Joe Coffee
  • Specialty Chocolate basket from the Milk Shake Factory, including a box of chocolate, milkshake vouchers, and more
  • $50 gift card to Larrimor’s
  • $50 gift card to love, Pittsburgh
  • $50 gift card to Heinz Healey’s
  • $50 gift card to 306 Forbes Boutique & Brow Bar
  • $50 gift card to Peter Lawrence
  • $25 gift card to Fresh Nostalgia
  • $30 gift card to Steel City
  • $25 gift certificate to The Headgear
  • $25 gift certificate to Inkwell at Oxford
  • $25 gift certificate to Boutique la Passerelle
  • $25 gift card to Kelly’s Sweets and Greets
  • $20 gift card to PG&H
  • $20 gift card to Market Street Grocery
  • $20 gift certificate to Oliver Flower Shop
  • $20 gift card to Nicholas Coffee & Tea Co.

Prizes subject to change without notice. Must be 18 years or older to enter. No purchase necessary to win. Winners in each category will receive a randomly assigned prize package.

New! Pass go and collect instant prizes
with Key Bank

There’s a new way to play Shopopoly! Stop by the Key Bank Oliver Avenue Branch to collect a random Community Chest or Chance card with instant giveaways inside, including gift cards, free merchandise from local stores, and more that you can win on the spot.

Limit one drawing per person. Giveaway subject to change without notice. Must be 18 years or older to participate. No purchase necessary to win.

How to Play

  1. Pick up a game board at any participating retailer or in Market Square.
  2. Pass Go and collect prizes: visit Key Bank to receive a Community Chest or Chance card for instant giveaways, while supplies last.
  3. Shop around Downtown collecting stamps as you visit different stores and pop-ups.
  4. Enter to win prizes by turning in your card by 4:00 p.m. at any stop or in Market Square.

Participating Businesses & Stops

Free Gifts with Purchase

Amplify your spending and receive a free gift or special deals with purchase from select retailers, while supplies last!

  • 306 Forbes Boutique & Brow Bar: first ten purchases will receive a free Hematite bracelet and 10% off your next purchase
  • Banner Coin Exchange: a free original $1 1957 or 1935 United States Silver Certificate with a minimum $10 coin or jewelry purchase
  • Boutique la Passerelle: Free pair of socks with a $50 purchase
  • Brooks Diamonds: free t-shirt and polishing cloth
  • Fresh Nostalgia: for any purchase $25 or more, receive a free mini rollerball perfume. If you spend $100 or more, receive a Fresh Nostalgia Scooter Graphic Logo Tee while supplies last
  • Heinz Healey’s: Free mystery gift while supplies last
  • Inkwell at Oxford: Free holiday ornament with a $10 purchase
  • Kelly’s Sweets and Greets: A free generous sample of chocolate-covered popcorn with any purchase of $10 or more
  • love, Pittsburgh: 20% off your purchase
  • Market Street Grocery: buy two bottles of wine, get one free
  • The Milk Shake Factory: Pittsburgh Penguins coloring books & colored pencils, while supplies last
  • Nicholas Coffee & Tea Co: Coupon for free cup of coffee and a Nicholas Coffee coffee scoopCoupon for free cup of coffee and a Nicholas Coffee coffee scoop
  • PG&H: A select handmade ornament
  • Rock ‘n’ Joe Coffee: Mystery envelope to the first 50 customers.
  • Sinful Sweets: Free chocolates with purchase
  • Steel City: Free mug for the first 10 people who make a purchase
  • The Headgear: a free knit hat (color of your choice) with a purchase of a $30 or more

Note: gifts with purchase are limited in quantity and available on a first-come, first-served basis. Additional restrictions may apply, check in with the individual store for more information.

🚗 Parking in Downtown is now easier than ever: on nights and weekends, parking in select garages is now only $3 so you can enjoy more of your favorite restaurants, stores, and activities. Learn more.


Downtown Made Easy Guide

Downtown Shopping Guide

State of Downtown Pittsburgh Report

Downtown Map

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