Brentwood Activities Guide: Winter 2024
Discover Brentwood’s exciting winter events, offering festive cheer for everyone! From parades and wine walks to carnivals, plan your memorable winter getaway today.
Welcome to winter in Brentwood! As the days grow shorter and a crisp chill fills the air, Brentwood transforms into a wonderland of festive activities and community spirit. This guide is your key to unlocking a memorable winter season, brimming with opportunities for joy, connection, and celebration.
Brentwood offers a diverse range of experiences, from enchanting holiday events like Santa visits and dazzling tree lighting ceremonies, to sophisticated wine walks and delightful culinary adventures. Whether you’re a local resident or planning a winter getaway, you’ll find something to captivate your heart and create lasting memories. The Community Enrichment Program actively works to maintain Brentwood’s beauty and quality of life, ensuring a welcoming atmosphere for all. Prepare to embrace the magic of winter in Brentwood!
Key Dates & Seasonal Highlights
Mark your calendars for a season of Brentwood brilliance! November 24th marks the start of Santa’s daily visits for photos, continuing through December 24th – even offering special pet photo opportunities! Keep an eye out for the exciting redevelopment project groundbreaking, celebrated by Mayor Meyer and the City Council on July 21, 2025.
January brings important updates, including the installation of a new stop sign at Upshur & 38th Street (effective January 31, 2024). Don’t miss the Winter Bizarre and Weed Warrior event on January 27, 2024. The Winter Wine Walk and Tasting Tour promises a delightful experience. Bubbles & Broomsticks adds a touch of magic to downtown Brentwood. These highlights, alongside ongoing community initiatives, ensure a vibrant and engaging winter season for all.

Holiday Events & Festivities
Brentwood sparkles with holiday magic! Enjoy tree lightings, festive readings, Santa visits, and captivating magic shows for a truly joyful season.
Santa Visits & Photo Opportunities
Create cherished memories with Santa this winter in Brentwood! Families have the wonderful opportunity to meet Santa Claus and capture those precious moments with professional photos. Santa will be making appearances daily from November 24th through December 24th, spreading holiday cheer throughout the community.
For pet lovers, select days and hours will be specifically designated for photos with your furry friends – a truly unique and heartwarming experience! Be sure to check the official website for detailed information regarding Santa’s schedule, operating hours, and pricing for photo packages. Don’t miss this chance to share the magic of the season with Santa and create lasting memories for years to come. Visiting Santa is a Brentwood tradition, and this year promises to be more magical than ever!
Tree Lighting Ceremonies
Experience the enchantment of the season at Brentwood’s annual Tree Lighting Ceremonies! These beloved events mark the official start of the winter holidays, bringing the community together in a celebration of light and joy. Gather with friends and neighbors as the magnificent tree is illuminated, creating a breathtaking spectacle for all ages.
While specific details regarding dates, times, and locations are yet to be announced, anticipate festive music, heartwarming performances, and perhaps even a special appearance by Santa Claus himself! These ceremonies are a cornerstone of Brentwood’s holiday traditions, fostering a sense of community spirit and wonder. Keep an eye on local event listings and the city’s website for updates and prepare to be dazzled by the twinkling lights and festive atmosphere. It’s a magical experience you won’t want to miss!
Holiday Parades & Community Celebrations
Join the festive fun at Brentwood’s Holiday Parades and vibrant Community Celebrations! These events showcase the spirit of the season with dazzling floats, marching bands, and cheerful performances. Experience the joy as local organizations and community groups come together to create a spectacular display of holiday cheer.
Brentwood’s celebrations are designed to bring families and friends together, fostering a sense of unity and goodwill. Expect lively music, captivating entertainment, and plenty of opportunities to spread holiday joy. While specific parade routes and celebration schedules are forthcoming, anticipate a delightful experience filled with wonder and excitement. Check the city’s official website and local event calendars for detailed information and prepare to be captivated by the magic of the season. Don’t miss out on these cherished Brentwood traditions!
Festive Readings & Magic Shows
Immerse yourself in the enchantment of the season with Brentwood’s Festive Readings and captivating Magic Shows! These events offer a delightful escape into a world of storytelling and illusion, perfect for families and individuals alike. Experience the wonder as talented performers bring beloved holiday tales to life through expressive readings and mesmerizing theatrical presentations.
Prepare to be amazed by skilled magicians who will astound audiences with incredible feats of illusion and sleight of hand. These performances are designed to spark imagination and create lasting memories. Specific venues and showtimes will be announced shortly, so keep an eye on local event listings and the city’s official website. Don’t miss the opportunity to experience the magic and joy these events bring to Brentwood this winter season!

Wine & Culinary Experiences
Savor Brentwood’s winter flavors with wine walks, tasting tours, and special restaurant menus! Enjoy unique culinary delights and local wine pairings this season.
Winter Wine Walk & Tasting Tours

Embark on a delightful journey through Brentwood’s vibrant wine scene this winter! The Winter Wine Walk & Tasting Tours offer a unique opportunity to sample exquisite local wines while strolling through the charming downtown area. Participants can explore various tasting locations, each showcasing a diverse selection of Brentwood’s finest vintages.
These tours aren’t just about the wine; they’re a celebration of community and local businesses. Enjoy the festive atmosphere, mingle with fellow wine enthusiasts, and discover hidden gems along the way. Many tours also feature pairings with delectable appetizers, enhancing the overall tasting experience. Don’t miss the chance to indulge in this sensory adventure and create lasting memories. Check event resources and websites for dates, times, and ticket information to secure your spot!
Local Restaurant Specials & Winter Menus
Warm up your winter with Brentwood’s diverse culinary scene! Local restaurants are embracing the season with special menus and enticing offers designed to delight your taste buds. From cozy cafes to upscale dining establishments, there’s something to satisfy every craving.
Expect to find seasonal ingredients featured prominently, with hearty comfort food and festive treats taking center stage. Many restaurants are offering prix fixe menus, perfect for a romantic dinner or a family gathering. Look out for special promotions, happy hour deals, and themed nights adding extra flavor to your winter dining experience. Explore Brentwood’s restaurants and discover unique winter creations – a perfect complement to your holiday festivities and a welcome escape from the cold!
Community & Enrichment Programs
The Community Enrichment Program fosters a healthy, safe, and attractive Brentwood, encouraging residents to actively improve neighborhoods and maintain property values.
Community Enrichment Program Overview
Brentwood’s Community Enrichment Program is a cornerstone of maintaining the city’s high quality of life. This vital initiative actively engages residents in collaborative efforts to enhance and preserve the beauty, safety, and overall appeal of our neighborhoods. City staff work hand-in-hand with community members, fostering a sense of ownership and shared responsibility.
The program’s core focus revolves around proactive neighborhood improvements, addressing concerns ranging from cleanliness and beautification to safety and property value maintenance. Through organized initiatives and collaborative projects, residents are empowered to take a direct role in shaping the future of their communities. This collaborative spirit not only strengthens neighborhood bonds but also contributes to a more vibrant and thriving Brentwood for all.
Neighborhood Improvement Initiatives
Brentwood’s commitment to neighborhood vitality is demonstrated through a variety of impactful improvement initiatives. These programs empower residents to actively participate in enhancing their surroundings, fostering a stronger sense of community pride and ownership. Initiatives range from organized clean-up events and beautification projects to collaborative efforts focused on maintaining property values and addressing local concerns.
Residents are encouraged to collaborate with city staff to identify areas for improvement and develop tailored solutions. These initiatives not only enhance the aesthetic appeal of neighborhoods but also contribute to increased safety and a higher quality of life for all Brentwood residents. Active participation is key to the success of these programs, ensuring a thriving and well-maintained community for generations to come.
Ongoing Winter Activities
Brentwood offers diverse entertainment, including parks, recreation, and indoor options. Explore local tips and discover exciting events throughout the winter season!

Parks & Recreation Opportunities
Brentwood’s parks remain a vibrant hub even during the winter months, offering a refreshing escape into nature. While specific winter programming details are still developing, residents can anticipate opportunities for leisurely walks, invigorating jogs, and peaceful moments amidst the serene landscapes. The city’s commitment to maintaining accessible outdoor spaces ensures that everyone can enjoy the benefits of fresh air and exercise throughout the season.
Keep an eye on the city’s official website for updates regarding potential winter-themed events within the parks, such as guided nature walks or festive scavenger hunts. Regular park maintenance will continue to ensure safe and enjoyable experiences for all visitors. Don’t forget to check for any temporary closures due to inclement weather conditions. Brentwood’s parks provide a wonderful opportunity to connect with nature and stay active during the colder months!
Indoor Entertainment Options
When the winter chill sets in, Brentwood offers a delightful array of indoor entertainment options to keep residents and visitors engaged and amused. Explore local venues hosting captivating performances, from live music and theatrical productions to engaging art exhibits and community events. Several businesses within Brentwood provide unique experiences, catering to diverse interests and age groups.
Consider visiting local arcades or bowling alleys for a fun-filled outing with family and friends. Numerous restaurants and cafes offer cozy atmospheres perfect for enjoying a warm beverage and a delicious meal. Check community centers for workshops, classes, and recreational activities designed to enrich and entertain. Brentwood’s indoor spaces provide a welcome respite from the cold, ensuring a vibrant and enjoyable winter season for all!

Redevelopment Project Updates
Mayor Meyer and the City Council broke ground on Brentwood’s anticipated redevelopment project with CenterCal Properties in July 2025, enhancing accessibility.
CenterCal Properties Redevelopment ─ Progress Report
The highly anticipated redevelopment project, a collaboration between Mayor Meyer, City Councilmembers, and CenterCal Properties, officially commenced on July 21, 2025, with a groundbreaking ceremony. This ambitious undertaking promises significant enhancements to the Brentwood landscape, aiming to create a more vibrant and accessible community space.
The CenterCal Properties team, comprised of dedicated management, leasing, maintenance, and other crucial personnel, is fully engaged in driving the project’s success. Initial phases are focused on foundational work and infrastructure improvements, laying the groundwork for future development. Regular progress updates will be provided to ensure transparency and community involvement.
The project’s design prioritizes pedestrian flow and accessibility, aiming to seamlessly integrate with existing winter event locations. Careful consideration is being given to minimize disruptions during the festive season, ensuring a positive experience for residents and visitors alike. The team is committed to delivering a revitalized Brentwood that benefits all.
Impact on Winter Events & Accessibility
The ongoing CenterCal Properties redevelopment is being carefully managed to minimize disruption to Brentwood’s beloved winter events. While construction progresses, the project team is prioritizing pedestrian safety and maintaining access to key event locations, including those hosting the tree lighting ceremonies and holiday parades.
Temporary adjustments to parking and traffic flow may be necessary during peak event times. Residents and visitors are encouraged to utilize available transportation options and plan accordingly. Detailed information regarding parking and accessibility will be communicated through the city’s website and event resources.
The long-term goal of the redevelopment is to enhance accessibility and create a more welcoming environment for all winter activities. Improved pedestrian walkways and expanded public spaces will contribute to a more enjoyable experience for everyone attending Brentwood’s festive celebrations. The team is dedicated to a smooth transition.

Important Notices & Updates (January 2024)
Please be aware of the new stop sign at Upshur & 38th Street, installed January 31st, 2024. Also, join the Winter Bizarre and Weed Warrior event!
New Stop Sign Installation ‒ Upshur & 38th Street
A new stop sign has been installed at the intersection of Upshur Street and 38th Street as of January 31st, 2024. This installation is a crucial safety measure implemented to enhance pedestrian and vehicular traffic flow within the neighborhood. Residents are urged to exercise increased caution when approaching and navigating this intersection, and to fully comply with all traffic control devices.
The City of Brentwood prioritizes the safety of its community members, and this addition reflects that commitment. Please familiarize yourself with the new signage and adjust your driving habits accordingly. We appreciate your cooperation in ensuring a safe environment for everyone. Further updates regarding traffic safety initiatives will be posted on the city website and through community notifications. Remember to always be alert and drive responsibly.
Winter Bizarre & Weed Warrior Event Details
Join us for a unique combination of community spirit and environmental stewardship at the Winter Bizarre & Weed Warrior event on January 27th, 2024! This exciting event offers a dual opportunity to engage with your neighbors while contributing to the beautification of Brentwood. The “Weed Warrior” portion focuses on removing invasive plants to support native flora, fostering a healthier ecosystem.
The “Winter Bizarre” component promises a fun-filled atmosphere with local vendors, unique crafts, and festive activities for all ages. It’s a fantastic way to discover local talent and find one-of-a-kind gifts. Volunteers are welcome for both aspects of the event – tools and guidance will be provided. Check the city website for specific times and meeting locations. Let’s make Brentwood shine this winter!

Planning Your Brentwood Winter Getaway
Brentwood welcomes visitors with diverse accommodations, easy transportation, and local tips for a perfect winter escape filled with events and cheer!
Accommodation Options
Brentwood offers a variety of lodging choices to suit every traveler’s preference and budget. From cozy bed and breakfasts providing a charming, intimate experience to well-known hotel chains ensuring consistent comfort and convenience, you’ll find the perfect base for your winter exploration. Consider exploring options in nearby towns for expanded availability and potentially different price points.
For those seeking a more extended stay or a home-away-from-home atmosphere, vacation rentals are readily available, offering amenities like full kitchens and separate living spaces. Booking in advance is highly recommended, especially during peak holiday periods, to secure your desired accommodation and potentially benefit from early-bird discounts. Don’t forget to check online travel agencies and directly with hotels for the best deals and availability. Prioritize locations offering easy access to Brentwood’s winter events and attractions for a seamless getaway!
Transportation & Parking Information
Navigating Brentwood during the winter season is generally straightforward, with several transportation options available. While public transportation serves the area, utilizing a personal vehicle offers greater flexibility, especially for accessing events outside the downtown core. However, be prepared for potential traffic congestion during peak event times and holiday shopping periods.
Parking in downtown Brentwood can be limited, particularly during popular events like the Tree Lighting Ceremony and Holiday Parades; Utilize designated parking lots and be mindful of street parking regulations to avoid citations. Consider ride-sharing services as a convenient alternative to driving and parking. Checking event websites beforehand can often reveal specific parking recommendations or shuttle services offered for larger gatherings. Planning your route and allowing extra time for travel and parking will ensure a stress-free experience!
Local Tips & Recommendations
To fully enjoy your Brentwood winter experience, embrace the community spirit and plan ahead! Dress warmly in layers, as temperatures can fluctuate. Check the weather forecast before heading out, especially for outdoor events. Don’t miss the opportunity to visit Santa for a memorable photo – and even bring your furry friends on select days!
Explore the local restaurants offering special winter menus and cozy atmospheres. Consider attending the Winter Wine Walk for a delightful tasting tour. For a unique experience, look into “Bubbles & Broomsticks” events. Remember to book accommodations in advance, especially during peak holiday periods. Finally, stay updated on event details and potential changes through official websites and local resources – ensuring a magical Brentwood winter getaway!
Event Resources & Websites
Stay connected and informed about all Brentwood winter happenings through these valuable online resources! For a comprehensive overview of events and festivities, begin your search with the official City of Brentwood website – a central hub for community information. Explore local event calendars to discover a wider range of activities, including performances and workshops.
Specific events, like the Winter Wine Walk, often have dedicated webpages with detailed schedules and ticket information. Keep an eye on local news outlets and community social media pages for up-to-date announcements and potential changes. Don’t forget to check the websites of participating businesses, such as restaurants and wineries, for special winter offerings. Utilizing these resources will ensure you don’t miss a single moment of Brentwood’s winter magic!