15 Holiday Stroll Ideas to Bring Shoppers Downtown

A holiday stroll is a promise to your merchants: put on a good enough night and the sidewalks fill, the doors open and the registers ring. The chambers and Main Street programs that keep that promise give people a reason to walk the whole district, not just the first block: Christmas Carolers on the corner, a Holiday Scrooge Character grumbling his way down the sidewalk, Frosty the Snowman outside the toy store and the Enchanted Sleigh Train Ride looping between the two ends of the street.

Here are 15 holiday stroll ideas grouped by the job each one does: drawing the crowd, keeping it moving along the street and keeping it shopping. Nearly every idea is rentable from the winter rentals collection at Perfect Parties USA, each comes with a planning tip on placement, timing or power, and the shops, vendors and permits stay with you, whether your district is a Massachusetts mill town or a village green in Connecticut.

Ideas That Draw the Crowd Downtown

One headline attraction gives the stroll a starting point and a reason to drive in.

1. Santa Arrives to Open the Stroll

Santa Claus: Santa opens the night with an announced arrival at one end of the district, then walks the first block with the crowd behind him. A posted arrival time brings families at the start of the stroll instead of the end, and the crowd that follows him is already walking past the shops. Add the Mrs. Claus rental, which its product page calls a festive rental piece, as a festive touch beside him, and confirm at booking what it includes. Planning Tip: Publish the arrival time on every flyer and post, and stage the arrival at the end of the district farthest from the main parking lot so the crowd walks the whole street to see him. Book Santa Claus.

2. SnowGlobe Live in the Square

SnowGlobe Live: A 15-foot-tall walk-in snow globe that families step inside for a photo, suitable for any age; its product page names municipalities and shopping malls among its best fits. It is the attraction people tell their neighbors about, and it handles about 90 guests an hour. Planning Tip: It needs a 25 by 25 foot space and a 30-minute setup, so put it in the central plaza or on the green halfway down the district, where families walking to Santa pass it twice. Rent SnowGlobe Live.

3. A Skating Rink on the Green

Synthetic Ice Skating Rink: A synthetic ice rink with no refrigeration, delivered with fencing and rental skates in assorted sizes, on the green or a closed side street. Skaters bring spectators, spectators get cold and step into the coffee shop, and the shops get the traffic. The smallest layout is 20 by 40 feet for up to 25 skaters at a time, and the synthetic ice rink rental guide covers sizing and setup. Planning Tip: Hand out free skate session tickets through the participating merchants, so a skate ticket is also a reason to walk into a store. Rent the Synthetic Ice Skating Rink.

4. Snowfall on Main Street

Snow Machine: A theatrical snow machine that turns a fluid into falling snow that does not accumulate, aimed over the busiest block. A snowfall at the top of every hour gives the crowd a reason to gather on that block, and the snow does not accumulate. The product page does not mention outdoor use, so confirm it at booking. Planning Tip: It needs one dedicated 20 amp circuit, so ask a merchant with a dedicated line near the window to host it in exchange for the crowd outside the door. Rent the Snow Machine.

Ideas That Keep the Crowd Moving Along the Street

A stroll works when the entertainment walks too, pulling people past every door.

5. Carolers on the Corners

Christmas Carolers: Four costumed Victorian carolers singing holiday favorites, moving from corner to corner on a posted schedule. Music on the corner tells shoppers where the stroll is happening and gives the sidewalk a sound. Planning Tip: Post their corner schedule in the shop windows, 20 minutes per corner, so shoppers walk to the next block to catch them. Book the Christmas Carolers.

6. Scrooge Working the Sidewalk

Holiday Scrooge Character: A strolling Scrooge who grumbles “Bah humbug” at passersby and, according to his product page, still manages to put people in the holiday spirit; the page lists store sales among the events he suits. Kids love being scolded by him, and their parents take the photo. Planning Tip: Give him a route past the stores running stroll-night sales, and let him complain about the bargains at every one. Book the Holiday Scrooge Character.

7. Frosty Outside the Toy Store

Frosty the Snowman: A costumed Frosty the Snowman character for the sidewalk, where families stop to say hello and take a picture. Little kids who are not ready for Santa are usually happy to wave at a snowman. Planning Tip: Station Frosty outside the family-friendly shops for the first hour, when the youngest kids are out, and plan for the 60-minute setup listed on the product page. Book Frosty the Snowman.

8. Holiday Entertainers Between Blocks

Holiday Entertainers: A holiday entertainers package for the gaps between the headline attractions. The product page does not name the characters or say whether they stroll or work outdoors, so confirm the lineup and the setting at booking. Planning Tip: Assign them to the quiet middle blocks, or a storefront there if they work indoors, where shoppers would otherwise turn back toward the car. Book the Holiday Entertainers.

9. A Sleigh Train Loop

Enchanted Sleigh Train Ride: A trackless train styled as a classic horse-drawn sleigh, carrying 4 to 6 guests at a time and about 60 riders an hour on a loop between the two ends of the district. The ride turns the long walk to the far end into the fun part, and families ride it back. Planning Tip: Run it on a closed side street or the plaza with a pickup at each end, and print the loop on the stroll map. Rent the Enchanted Sleigh Train Ride.

10. The Stroll Passport

A passport card that shoppers get stamped at each participating shop and turn in for a drawing at the end of the night. A passport is the simplest way to move people past the first block, and it gives merchants a reason to greet everyone who walks in. Use a Prize Wheel at the last stop so every finished card wins something small on the spot. Planning Tip: Require stamps from at least one shop on every block, and draw the grand prize at the stroll’s last attraction so the crowd stays until closing.

Ideas That Keep Them Shopping

Photo stops and warm-ups belong in front of the stores, not in the middle of the green.

11. A Sleigh Selfie at the Anchor Store

Santa Sleigh Selfie: A Santa sleigh photo prop where families take their own holiday picture, about 60 guests an hour. Put it in front of the anchor store, and every photo that gets posted has the shop’s window in the background. Planning Tip: It needs a 15 by 12 foot footprint with 12 feet of height and one dedicated 20 amp circuit, so pick the storefront with the widest sidewalk and an outlet inside the door. Rent the Santa Sleigh Selfie.

12. Santa Photos in an Empty Storefront

Santa Photos: A Santa photo set with a Santa chair, red carpet, stanchions, photo equipment and holiday props, with an instant printed photo for every guest. An empty storefront becomes Santa’s workshop for the night, and the line out the door shows passersby where the action is. The page notes that Santa is priced separately based on availability. Planning Tip: The set needs a 10 by 10 foot footprint with 12 feet of height and one dedicated 20 amp circuit, so confirm the ceiling height of the storefront before you book. Book Santa Photos.

13. A Gondola Photo Booth

Gondola Photo Booth: A winter scene built around a gondola lift from the Alps, where guests put on winter hats, goggles, scarves and skis and pose on an actual gondola for a souvenir photo. It turns a bank lobby or a vacant shop into a destination, at about 45 guests an hour. Planning Tip: Allow the 90-minute setup, a 12 by 12 foot space and one dedicated 20 amp circuit, and set it up the afternoon before if the host business allows. Rent the Gondola Photo Booth.

14. Hot Chocolate on the Middle Block

Hot Chocolate: A hot chocolate station placed on the block that needs the most foot traffic. A cup in hand slows the walk past every window, and warm hands keep people outside longer. The product page does not list what the station includes, so confirm cups and servings at booking. Planning Tip: It fits an 8 by 3 foot space, so ask the merchant in the middle of the district to host it beside the door. Rent the Hot Chocolate station.

15. Personalized Ornaments to Take Home

Personalized Ornaments: A professional calligrapher hand-writes names on 3-inch satin-finish ornaments printed with your logo, finished with a metallic cap and a gold hanging cord, so every family leaves with a keepsake from the stroll. Print the business association’s logo or a sponsor’s, and the ornament hangs on a tree all season. Planning Tip: It fits a 6 by 6 foot space with a 15-minute setup, so put it inside the sponsor’s shop and let the line wait among the shelves. Rent the Personalized Ornaments.

How to Plan a Holiday Stroll Lineup

Match the lineup to the length of your district and the size of your crowd. A village stroll of three or four blocks runs well on Santa, the carolers, Scrooge, one photo stop and a hot chocolate station. A longer downtown adds a headline attraction at the far end, the sleigh train loop to carry people back and holiday entertainers for the quiet middle blocks. A business district expecting a few thousand shoppers can add the skating rink, which keeps families downtown for an extra hour. Many strolls open with a lighting, so the tree lighting event rentals page and the tree lighting ceremony ideas list cover that part of the night.

As a rule of thumb, plan one performer or attraction for every block of the stroll and one headline attraction per 1,000 guests, and put every photo stop in front of a participating shop. Book six to eight weeks ahead, as early in November as you can, because strolls across Massachusetts, Connecticut and Rhode Island fall on the same December weekends as the tree lightings. If the stroll ends at a market, the holiday market ideas list covers the stalls, and the Christmas festival ideas guide shows how to turn the night into a full festival.

Rent Holiday Stroll Attractions From Perfect Parties USA

Perfect Parties USA is based in Peabody, Massachusetts and owns hundreds of attractions, including every rentable item on this list, so the games you book are the games that arrive, maintained and ready to play. Every rental includes delivery (fees based on your address), professional setup, trained attendants and prizes for staffed games, and complete teardown. We are fully insured, with a certificate of insurance available for venues and schools, and we have produced events of every size across New England and the Northeast for decades, from Massachusetts, Boston, Connecticut and Rhode Island to New Hampshire and New York.

Ready to get this party started? Contact Perfect Parties USA to talk to one of our Party Pros. Request a Quote.

Frequently Asked Questions

What is a holiday stroll?

A holiday stroll is an evening when a downtown or business district stays open late in December, with entertainment, photo stops and warm-up stations along the street to bring shoppers in. Chambers of commerce and Main Street programs run them to fill sidewalks and shops, and the best ones spread the attractions along the whole district instead of one corner.

What are the best holiday stroll ideas to bring people downtown?

The best holiday stroll ideas give people a reason to walk the whole district: Santa arriving at the far end, carolers and a strolling Scrooge moving between corners, a sleigh train loop, a passport card stamped at participating shops, and photo stops in front of the stores. Perfect Parties USA rents the performers and attractions for strolls across Massachusetts and in neighboring states.

Are holiday stroll attractions good for kids?

Yes, holiday stroll attractions suit families with kids of every age, which is who most strolls want downtown. Toddlers do well with Frosty and the sleigh train, school-age kids love Santa, the sleigh selfie and Scrooge, and teens and adults take to the skating rink and the gondola photo booth. Plan the attractions for little kids in the first hour of the night.

What is included when you rent stroll entertainment from Perfect Parties USA?

Every rental from Perfect Parties USA includes delivery (fees based on your address), professional setup, trained attendants and prizes for staffed games, and complete teardown, with every unit cleaned and sanitized. The photo sets come with their props, an outdoor date can be rescheduled for rain at no charge with 24 hours notice, and a certificate of insurance is available for the town or the business association.

Where should attractions go along a holiday stroll route?

Put the headline attraction at the end of the district farthest from the main parking, photo stops in front of participating shops, warm-up stations on the quietest middle block and strolling performers in the gaps between them. That spread moves the crowd past every door, which is the whole point of the stroll for the merchants who host it.

Does Perfect Parties USA provide holiday stroll entertainment in Massachusetts?

Yes, Perfect Parties USA provides holiday stroll entertainment across Massachusetts and in Connecticut, Rhode Island, New Hampshire and New York, including Santa Claus, carolers, Scrooge, Frosty, the Enchanted Sleigh Train Ride, the synthetic ice rink and photo stops. The company is based in Peabody, Massachusetts; confirm delivery to your town with the quote.

How far in advance should you book entertainment for a holiday stroll?

Book holiday stroll entertainment six to eight weeks ahead, and earlier for Santa, the sleigh train and the skating rink, because strolls and tree lightings across New England fall on the same few December weekends. Booking early with Perfect Parties USA also leaves time to plan the route, confirm power with the host merchants and print the stroll map.