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Celebrate the Season on River Street.

December 4 

December 5 - 30 


Merry n Bright

The Village of Montgomery and the Greater Montgomery Area Chamber of Commerce hosts its annual Tree Lighting in front of the Village Hall on the first Sunday in December. The event features Santa Claus's prompt arrival at 5P by the Montgomery-Countryside Fire District fire engine, musical performances by area school children and local singers, strolling carolers, free hot chocolate and cookies, kids giveaways, and a coloring contest sponsored by local River Street businesses. Participants should dress for the weather as most activities are outdoors. 

In addition to lighting the tree outside Village Hall, the Festival of Trees kicks off which includes trees decorated by residents, families, businesses, and organizations both indoors at Village Hall and outdoors along River Street (between Webster & Mill). 

All are invited. Bring the family to meet Santa, he arrives promptly at 5P and will be onsite until 7P for visits and pictures. Area residents are invited to bring the whole family to meet Santa, have cookies and cocoa and vote for their favorite tree. For those unable to attend the Sunday event, the Festival of Trees will stay during the month of December. Indoor trees will be available for viewing during business hours at Village Hall 8A-4:30P Monday through Friday.


Village Hall (200 N. River St.)
- Visit with Santa
- Listen to the Oswego East Tri-M Honor Society
- Enjoy acapella singing from Oswego East High School
- Stroll the building and view the Festival of Trees submissions from local community groups and businesses
- Stop in the Multi-Purpose Room for free crafts and write a letter to Santa with the volunteers from the Rotary Club of Montgomery and listen to the Oswego East A Capela Jazz Ensemble

Atrevete Confections (216 N. River St)
Stop by Atrevete, take in the smells of their delicious pastries, and grab a free 6oz hot chocolate or splurge on one of their custom coffee creations!

Gray's Mill Estate (211 N. River St.)
Stop in Danny Boy's and pick up your free cookie bag to nibble on while you stroll
- The restaurant and bar will be open this evening. Make reservations in advance if you want to stay for dinner!

Farmers Insurance- Ryan Watson (109 N. River St.)
Meet Ryan and his family out front to pick up your festival glow giveaway

Montgomery Economic Development Corporation & Best Homes Fox Valley (200 Webster St.)
Swing into the MEDC & Best Homes Fox Valley to enter the Kids Coloring Contest*
- Kids 12 and under can color onsite or take their pages and crayons home and bring their entry back before December 13 to enter to win prizes
*Kids Coloring Contest submissions will be on display at Village Hall throughout December

River Street Stage (centrally located near the VFW Post 7452 Parking Lot)
4:30 - 5:00P | Get festive in the street with holiday music by local DJ Tony Rios of Titan Sound Entertainment
Approximately 5P | Santa's Arrival & Tree Lighting
5:15P | Welcome
5:20P | Oswego East A Capella Jazz Ensemble
5:40P | Nicholson Elementary School
6:00P | McDole Elementary School
6:20P | Carols by Grace sponsored by Gray's Mill Estate
6:40P | Live Performance by professional carolers, the Festive Singers

2021 Event Sponsors

Comed Powering the holidays
Ozinga Sponsor
The Lakone Company
MetroNet Sponsor

Sponsorship Opportunities are Available.
Spread holiday cheer and support the Montgomery community. Sponsor support goes directly back into the event to cover the cost of entertainment, add more lighting displays, and provide additional giveaways and activities for the community in the future years.

Email or call 331-212-9010 for more information.


Sponsor the Event


New Outdoor River Street Live Tree Sponsor
Fee $100 | Must provide outdoor weather-proof décor and lighting

Feature your business or organization from December 5 through 30 along River Street for all to see. This is a great way to show support of the Montgomery community and to showcase your brand for all who attend the Tree Lighting, visit River Street, or come to see the River Street Lights during December. The fee includes a 5-6' Douglas Fir purchased from local Schaefer's Greenhouse and includes installation, staking, and watering by Village of Montgomery Public Works. Additionally, all outdoor tree sponsors will receive a 24"x18" corrugated sign with their logo to be staked in front of their tree and have a chance to win the 2021 Mayor's Choice Award. 

Decorating must take place between December 1 beginning at 8:30A and complete by December 5 at noon. More information


Register for River Street Festival of Trees

Traditional Indoor Artificial Tree Sponsor
Fee $0 | Must provide tree, decor, and lighting

The Village will continue to offer the traditional indoor tree festival complete with community voting as in years past. Participation in this contest is a great way to showcase your business or organization and support Montogmery indoors at Village Hall to showcase to all who attend the Tree Lighting or visit Village Hall between December 5-30. There is no fee for participation, but space is limited to 25 trees. Participants must provide a minimum 5', maximum 9' artificial tree, with decor and lighting. An 8.5"x11" sign will be distributed to each group to incorporate into your tree decor for proper labeling for the contest.

Tree decorating must take place between the hours of 8A-4:30P December 1, 2, or 3. More information here.


Register for Village Hall Festival of Trees


The Holiday Coloring Contest is sponsored by the Montgomery Economic Development Corporation (MEDC) and Best Homes Fox Valley. They will be open the night of the Tree Lighting for artists to pick up their coloring contest pages in person and color on-site if they choose! So be sure to stop by December 5 between the hours of 5-7P to their location at the corner of River & Webster. 

Montgomery Holiday Coloring Contest Rules

- There are two picture options available for coloring for each age category. Participants can pick whichever one they prefer to color. 
- Pictures are available to be downloaded on this site below. They can be picked up the evening of the Tree Lighting from MEDC & Best Homes office located on 200 Webster St. or can be picked up from their location or Village Hall after the December 5 event. 
- All entries are due for judging on December 13 by 5P. Entries will be hung as they are received on the windows of Village Hall facing River Street for all to view. 
- Winners will be contacted by December 30. 
- Please be sure to list artist names and parent or guardian contact information on the back so winners can be appropriately notified. 
- One winner will be selected from each age group and will win a craft-themed prize courtesy of the contest sponsors. 
- Categories are Ages 5 & Under, Ages 6-9, and Ages 10-12. 
- One entry is allowed per child.
- Entries can be picked up, dropped off, or mailed to one of the following locations: 1) MEDC/Best Homes 200 Webster St. or 2) Village Hall 200 N. River St.

Questions? Call Char with the MEDC at 815-703-1338 or contact her via email at

Ages 5 & Under
Ages 6-9
Ages 10-12