Paws, Pints & Pumpkins: Doggoween Returns to Bay Meadows!

Fall is in the air, and one of Bay Meadows’ most beloved four-legged traditions is back! Fieldwork Brewing San Mateo’s annual Doggoween celebration returns Saturday, October 31, from 12–2 p.m., bringing costumed pups, proud pet parents, and neighborhood friends together for an afternoon of Halloween fun in the beer garden. From creative canine costumes to delicious food, craft beer, and plenty of tail wags, this festive gathering has become a cherished autumn tradition that celebrates the playful, welcoming spirit of our San Mateo neighborhood.

The highlight of Doggoween? The always-entertaining dog costume contest and parade! Whether your pup is dressed as a pint-sized pumpkin, a superhero, or something wonderfully unexpected, it’s their moment to shine. To participate, dogs must be signed in at the Fieldwork taproom, arrive in costume, and join the parade. Winners are selected by popular vote, so bring your friends, family, and fellow dog lovers to cheer on your favorite furry contestants. The top three pups will take home Fieldwork gift cards: $50 for first place, $25 for second, and $10 for third. Even if your dog prefers watching the festivities from the sidelines, there’s plenty to enjoy while soaking up the autumn atmosphere in Fieldwork’s lively, open-air beer garden.

Of course, the fun doesn’t stop at Fieldwork. Bay Meadows is a neighborhood where dogs are part of the community, and daily adventures are always close to home. With 18 acres of parks and open space, tree-lined streets, neighborhood pathways, and connections to the San Francisco Bay Trail, there are plenty of opportunities to get outside with your four-legged companion. Enjoy a leisurely morning stroll past Paddock Park, explore the neighborhood’s green spaces, or take a longer walk along the Peninsula’s scenic trails. For residents of the Apartment Collection at Bay Meadows, pet-friendly living makes it even easier to share everyday moments with the furry members of the family. It’s a lifestyle that encourages fresh air, friendly encounters, and spontaneous conversations with neighbors—often sparked by an enthusiastic wagging tail.

What makes Doggoween especially memorable is the sense of community that brings everyone together. Fieldwork’s beer garden in Bay Meadows Town Square is already a favorite gathering place for neighbors, coworkers, families, and friends, and this annual celebration adds an extra dose of seasonal fun. Whether you’re a Bay Meadows resident, a Peninsula local, or simply visiting with your pup, mark your calendar for Saturday, October 31, from noon to 2 p.m. Come for the costumes, stay for the camaraderie, and raise a glass to another wonderful autumn in Bay Meadows. After all, some of the best neighborhood traditions are the ones we share with our dogs.

Bay Meadows October Agenda

October brings crisp fall days, festive nights, and plenty of reasons to explore the Peninsula. From pumpkin season and Halloween celebrations to outdoor markets, art festivals, hands-on workshops, and community traditions, the calendar is packed with ways to celebrate autumn close to Bay Meadows.

Get into the spirit with Nightfall at Filoli, the Half Moon Bay Art & Pumpkin Festival, haunted happenings at Hiller Aviation Museum, and trick-or-treating throughout the Peninsula. Or slow things down with a farmers market stroll, a scenic hike, a baking class, or a Saturday spent browsing local makers. With so much happening in San Mateo and beyond, October is the perfect time to get out, connect, and enjoy everything the season has to offer. We want to see your season! Show us your spooky decorated stoops, the stunning colors of our neighborhood landscape, your fall harvest in Persimmon Park, plus favorite seasonal sips at Blue Bottle Café and bites in Town Square.

Be sure to invite us to collaborate and tag us at @baymeadowslife in your autumn Instagram photos this fall.

When you live just steps from Caltrain, getting from here to there is easy and car-free. Grab the Hillsdale Caltrain schedule and dive into our monthly event roundup to discover all the ways to celebrate, create, explore, and connect throughout the month ahead.

Bay Meadows Run Club with Basecamp San Mateo. Join this free fun run Wednesday evenings at 6pm and Saturday mornings at 8am. Meet at 3050 S. Delaware for a 2-, 3-, 4- or 6-mile loop (something for everyone) to get moving. Run, jog, or walk. Happening weekly – rain or shine. All paces and people are welcome. Members often gather in Town Square for a Blue Bottle coffee or at Fieldwork Brewing Beer Garden after each run. Plus, there’s no fee! You heard right – membership is not required. This is a community building fun run, compliments of our neighbors at Basecamp Bay Meadows.

Sunday Downtown San Mateo Farmers Market. West Coast Farmer’s market runs year-round at 222 East 4th Avenue Sundays from 9am to 2pm in Downtown San Mateo. The farmer’s market has a curated selection of fresh fruits, veggies, and a couple of tasty food trucks to fuel your morning stroll.

College of San Mateo Farmers’ Market. Shop seasonally and fresh each Saturday from 9am to 1pm (year-round) at San Mateo’s largest farmer’s market located at 1700 West Hillsdale Boulevard.

The 25th Avenue in San Mateo Farmers’ Market. May through October 20 on Tuesdays from 3pm to 7 pm, this farmers market is an easy walk or bike ride from Bay Meadows (~0.8 mi), bringing the best Peninsula produce and makers moments from your door.

October 1- Nov 13, Cans for Change by Rise by Bozzuto. 🍁In the spirit of giving back, Rise by Bozzuto’s mission is to tackle hunger this holiday season. 🥫Join The Apartment Collection at Bay Meadows as they host a food drive to collect canned goods to support the San Francisco Marin Food Bank. Starting, Thursday, October 1st, through Friday, November 13th, you will have the opportunity to drop off your donations.

Participating is as easy as purchasing new, unopened canned goods and dropping them off in The Russell Leasing Office.

📍 3098 Kyne Street West, San Mateo, CA 94403
650-855-8768 | BayMeadows@bozzuto.com

October 2, First Friday Nights. On the first Friday of every month, from 5 PM until 8 PM, parents and kids celebrate together at CuriOdyssey in San Mateo. Dance to some of your favorite hits, while enjoying animal presentations and science activities.

October 2, Movies in the Park. Catch School of Rock under the stars at Barrett Community Center in Belmont, with movie snacks, raffle prizes, and plenty of outdoor movie night fun.

October 2, San Mateo County History Museum FREE First Fridays. Visit the SMCHM every Friday for free First Friday events, where children enjoy special programs including crafts and storytime, and adults can join a docent-led tour of the museum.

October 4, Autumn Succulent Terrarium Workshop. Create a festive pumpkin-shaped succulent terrarium, perfect for your autumn décor, at this hands-on seasonal workshop in San Mateo.

October 6, Marsh Hike at Coyote Point. Explore Coyote Point’s vibrant wetlands in San Mateo on a guided CuriOdyssey hike featuring native plants, local wildlife, and seasonal discoveries.

October 10 & 11, San Carlos Art & Wine Faire. Discover handcrafted art, local flavors, wine, brews, live entertainment, and family fun at the 34th Annual Art & Wine Faire in downtown San Carlos.

October 11, Croissant & Pain au Chocolat. Learn the art of classic French croissants and pain au chocolat in a hands-on baking class at Baking Arts in San Mateo.

October 17, HEAD WEST Marketplace. Spend the day exploring Downtown San Mateo’s B Street during the HEAD WEST Marketplace, where you can shop handcrafted goods from local makers and artists while enjoying the neighborhood’s vibrant retail shops and dining scene.

October 17–18, Half Moon Bay Art & Pumpkin Festival. Celebrate fall at the 54th Annual Half Moon Bay Art & Pumpkin Festival, kicking off with the legendary World Championship Pumpkin Weigh-Off.

October 23-November 1, Halloween Haunted Hangar. Come in costume and see the Gallery decked out in its spooky Halloween decorations and the “Great Pumpkin” Scavenger Hunt at the Hiller in San Carlos.

October 24, Belmont Centennial Fest. Celebrate Belmont’s 100th birthday at Twin Pines Park with a car parade and show, live music, food trucks, games, a time capsule ceremony, and an evening drone show.

October 24, Boos and Brews on B Street.Celebrate Halloween at Boos on B Street in Downtown San Mateo with trick-or-treating, crafts, music, food, and festive photo ops along the B Street Pedestrian Mall.

October 24, Halloween Spooktacular. Enjoy a spooktacular day in Redwood City with carnival games, a monster maze, creepy crafts, a haunted ambulance, mini pumpkin patch, prizes, and more Halloween fun.

October 28, Belmont Boo Bash. Celebrate Halloween at Belmont’s Boo Bash with Trunk or Treat, a haunted house, live music, food trucks, and festive fun for all ages in Belmont.

October 29, Trunk or Treat. Get ready for a spooktacular evening at the Hiller Aviation Museum’s Trunk or Treat in San Carlos, part of our annual Halloween Haunted Hangar celebration.

October 31, Doggoween at Bay Meadows. It’s back! And, it’s on Halloween! Get your dogs in costume and head to our neighborhood beer garden at Fieldwork Brewing San Mateo for a chance to WIN. The whole community comes together for this annual event. Follow Fieldwork_SanMateo and BayMeadowsLife on Instagram for more information.

October 31, Pumpkin Drop.Join a special celebration of Halloween excitement as the Hiller Aviation Museum’s witch drops her doomed pumpkin from a high flying helicopter at the Hiller in San Carlos!

Thru November 1, Nightfall. Step into Filoli after dark for a haunting Halloween adventure filled with pumpkins, firelight, mysterious clues, an enchanted mansion, glowing woodlands, and a hidden witch’s village.

Sep-Oct Sessions at Clayroom. When signing up for 6-week classes, one signs up by selecting (signing up for) the 1st class. Classes 2-6 will occur on a weekly cadence during the same day of the week and timeslot. 6-week in-studio classes for pottery.

Discount Tuesday (at Cinemark Century San Mateo 12). There’s never been a better time to turn up on a weekday, because every Tuesday at Cinemark is Discount Tuesday—cheap movie tickets are always within reach.

Bel Mateo Bowl Friday, Saturday and Sundays in San Mateo.
Karoake – Fridays from 7:30 – 11:30pm hit the mic with friends for some Karaoke.
Planet Bowling – Bowl in the dark under black lights on Fridays from 9:30 – 11:30pm and Saturdays from 8- 11:30pm.
Incredibowl – Fridays 9:30 – 11:30pm and Saturdays from 8 – 11:30pm interactive graphics elevate your bowling game with Incredibowl.
Family Pizza Night – Sundays from 5-8pm Family Pizza Nights and all you can bowl 8-10pm!
All You Can Bowl – Sundays enjoy unlimited bowling for 2 hours 8- 10pm! 

Bicycle Sundays. From 9am – 3pm, a 3.8-mile segment of Cañada Road along Crystal Springs Regional Trail is closed between the Filoli entrance and Highway 92 allowing for non-motorized activities including jogging, bicycling, hiking, roller-skating, and walking. Cañada Road between Edgewood Road to the Filoli entrance will remain open to vehicles. Check for holiday closures.

Experience Midurban life. Bay Meadows is a family-friendly neighborhood with lots of open space to enjoy all-year long. Whether it’s growing your own vegetables in an organic community garden, playing a game of pick-up basketball after work, team building over bocce in the beer garden, picnicking with family on warm summer nights or with a run around the park, there’s no shortage of green space to explore. Check out life out and about at Bay Meadows by following us on Instagram.

A New Trail to Explore: Skyline Watershed Ridge Trail Opens on the Peninsula

Living on the San Francisco Peninsula means having some extraordinary outdoor escapes within reach—and there’s a brand-new one to add to your weekend list. The Skyline Watershed Ridge Trail officially opened on August 24, 2026, introducing nearly six miles of new trail through the San Francisco Public Utilities Commission’s carefully protected 23,000-acre Peninsula Watershed. The trail begins just south of the intersection of Highways 35 and 92 and travels along the ridgeline through grasslands, wetlands, coastal scrub, Douglas fir forest, and redwood groves. Along the way, hikers, runners, cyclists, and equestrians can take in expansive views toward Crystal Springs Reservoir, San Francisco Bay, and the Pacific Ocean. It’s exactly the kind of close-to-home adventure that makes living at Bay Meadows—and on the Peninsula—so appealing.


This isn’t simply a pretty place to take a walk. The Skyline Watershed Ridge Trail is the newest segment of the larger Bay Area Ridge Trail, an ambitious regional vision for a continuous trail tracing the ridgelines surrounding San Francisco Bay. Ten interpretive panels along the new route turn an afternoon outside into an open-air classroom, sharing stories about local plants and wildlife, watershed stewardship, and the Hetch Hetchy Regional Water System. The six-foot-wide crushed-rock trail offers a combination of easier stretches and challenging hills and curves, with approximately 1,500 feet of elevation gain when traveling north to south. While the new trail is approximately six miles long, it’s currently out-and-back with no through connections, meaning adventurers who travel its entire length should prepare for a roughly 12-mile round trip. A future connection to Purisima Creek Redwoods Preserve is also in the planning stages.

Consider this your opportunity to unplug for a few hours. Pack plenty of water, sunscreen, a snack, and perhaps binoculars, then leave the everyday routine behind for a landscape that, until now, has had highly restricted public access. A free annual permit is required, is available for immediate use, and covers a permit holder and up to six guests. Parking is also free and first-come, first-served at the Highway 35 trailhead, with gates open daily from 6 a.m.–6 p.m. One important note for Bay Meadows’ many dog lovers: leave your four-legged hiking partner at home for this adventure. Dogs, including leashed dogs, aren’t permitted in order to protect sensitive habitat, wildlife, and drinking-water quality. There is also no potable water, no trash service, and no picnic tables along the route, so arrive prepared and pack out everything you bring. Cyclists should note that e-bikes and other motorized devices aren’t permitted; given the crushed-rock surface and steeper sections, mountain-terrain-appropriate bikes are recommended.

Back at Bay Meadows, that same connection between movement, open space, and everyday life is woven right into the neighborhood. With 18 acres of parks and open space, pocket parks, playgrounds, walking and biking paths, and direct connections to the San Francisco Bay Trail, getting outside doesn’t have to wait for the weekend. A morning walk through the neighborhood, an afternoon bike ride, or a family outing can all be part of the routine—and now the Skyline Watershed Ridge Trail gives residents another remarkable Peninsula destination to explore when they’re ready to go farther. It’s one more reason we love our San Mateo home base: city conveniences when you want them, with some of Northern California’s most beautiful open spaces waiting when it’s time to unwind, unplug, and reconnect with nature.

Before you go: Get your free annual permit, download the trail map, check current conditions, and plan your turnaround point before setting out. Bring all the water you’ll need, prepare for changing weather and exposed stretches, and remember that the full trail means a 12-mile round trip.  Great resources for this adventure can be found here and here.

Introducing The Morgan San Mateo at Bay Meadows

Make a move to The Morgan. Expansive, light-filled spaces featuring inspired interiors by Heather Hillard Design, abundant amenities and intimate landscaped courtyard retreats all welcome you home to Bay Meadows. Select from 2- and 3- bedroom expansive open-plan flats that offer exquisitely detailed spaces to connect and unwind – most offer separate dens tailor-made for work or play.

As our homes have become the center of daily life, having the right space matters more than ever. From room to work and bake together to peaceful retreats for recharging after a busy day, The Morgan offers everything you need to feel right at home.

Most flats boast separate dens tailor-made to be whatever kind of space you crave most.

Home office? Play room? Entertainment center? Yoga studio? Dog den?

The choice is yours. Find your perfect match at Bay Meadows by visiting available plans here.

Re(treat) yourself daily. Relish in your own personal hideaway. The Morgan’s Master Suites include dual walk-in closets, luxurious soaking tubs, and stand-alone, step-in frameless glass showers.

Stretch your legs at home or in the neighborhood. Bask in the sun or dine under the stars in your very own private outdoor space with room enough to unwind and enjoy. Perfect for keeping company with a just poured cup of coffee or a few close friends. Or venture to the stunning, open-air Mediterranean-inspired landscaped courtyard to join the conversation around the fireplace.

Enjoy 18 acres of parks outside your door or private outdoor space all your own, welcome home to The Morgan. Enjoy a walk, job or bike ride around the neighborhood with miles of trails connecting to the SF Bay Trail and beyond or plan a picnic in one of our neighborhood pocket parks. Spend your days growing fresh flowers, herbs and foraging a seasonal bounty at Persimmon Park, Bay Meadows’ Community Garden. Plots are available to rent by reservation on a first come, first serve basis.

Exquisite living extends beyond your private refuge to an amenity-rich oasis including, a clubroom, library, game room, secret gardens, hotel-inspired fitness studio, pet spa, bike room and more.

Bay Meadows Neighborhood Bike/Jog Trails Lead to The Bay Trail

Persimmon Park Community Garden at Bay Meadows

Conveniently located between San Francisco and Palo Alto in San Mateo, Bay Meadows offers housing within walking distance of Caltrain. Ease of transportation is only one reason you’ll fall in love with Bay Meadows. Smartly-designed, high-quality residences sit among 18 acres of open space, which includes parks, a community garden, public art, ball fields, bocce and basketball courts and a new playground. All this just a walk from Whole Foods, Clayroom San Mateo, Basecamp, LFBA, Sidewalk Juice, Bahche, The Breakfast Club at Midtown, Blue Bottle Coffee, Fieldwork Brewing Co., Hillsdale Shopping Center and more. Learn more about what Midurban life offers by following our Instagram feed and Facebook page.

 

 

Rock the Block Live Concerts at Hillsdale Shopping Center

There’s nothing quite like strolling from Bay Meadows for an evening of food, friends, and live music. Rock the Block is back at Hillsdale Shopping Center, and it’s your September weekend ritual waiting to happen. Free concerts every Friday from 6-8pm at the North Block Plaza make for the perfect way to wind down and connect.

Starting Friday, September 4 through September 25, gather under the open sky with your neighbors and enjoy some of the best local music around. Here’s who’s playing in September 2026:

September 4: Mike Annuzzi

September 11: UFO UFO

September 18: Top Secret

September 25: K-Pop DJ

Since Bay Meadows is just a short walk from Hillsdale, these concerts are more than an event—they’re a chance to make the neighborhood feel more like home. Here are some ways to make the most of the nights:

Stop by Bahche Mezzehouse & Wine Bar in Bay Meadows’ Town Square after work before a concert for Mediterranean Mezzes paired with your favorite glass or wine or beer or get a Souvlaki to-go. Bring a blanket and picnic under the stars, or grab food and drink to go from Hillsdale. Some great spots on North Block to check out are Shake Shack, Jamba Juice, Palette Tea Garden, Pinstripes, Mikiya Wagyu Shabu House, and The Refuge. If you’re up for exploring more, the Dining Terrace offers several options so you can mix and match.

Picture this: post-work walk from Bay Meadows, find a good picnic spot, listen to live music, maybe grab some souvlaki, a burger, or a bubble tea, and enjoy time with friends or family under the evening sky. It’s the kind of fall moment we live for.

And the best part…it’s free and open to all.

Rock the Block Hillsdale
Photo Credits: Hillsdale Shopping Center

Conveniently located between San Francisco and Palo Alto in San Mateo, Bay Meadows offers housing within walking distance of Caltrain. Ease of transportation is only one reason you’ll fall in love with Bay Meadows. Smartly-designed, high-quality new homes and The Bay Meadows Apartment Collection sit among 18 acres of open space, which includes parks, a community garden, public art, ball fields, bocce and basketball courts and a new playground. All this just a walk from Hillsdale Shopping Center, Whole Foods, Sidewalk Juice, Blue Bottle Coffee, The Breakfast Club at Midtown San Mateo, Bahche Mezzehouse & Wine Bar, LFBA Studios, Basecamp San Mateo, Clayroom San Mateo, Fieldwork Brewing Co. and more. Learn more about what Midurban life offers by joining us on Instagram.

 

Summer Days 2026: A Weekend of Fun Just Minutes from Bay Meadows

Summer is still in full swing, and one of the Peninsula’s favorite community celebrations is returning to Foster City. Foster City Summer Days 2026 takes over beautiful Leo J. Ryan Park, 650 Shell Boulevard, August 14–16 for a free, family-friendly weekend filled with live music, carnival rides, local vendors, food, and plenty of reasons to get outside. Now in its fourth year, the festival is an easy summer outing from Bay Meadows, with Leo J. Ryan Park just a short drive or bike ride from the neighborhood.

Friday evening kicks things off with a classic car show along Shell Boulevard from 4–7 p.m., followed by carnival rides and games from 5–10:30 p.m. Food trucks and beverage booths will be open from 5–8 p.m., and Mercy and the Heartbeats takes the stage at the Leo J. Ryan Park Amphitheater from 6–8 p.m. On Saturday, the festival expands with carnival rides from 11 a.m.–11 p.m., a craft vendor marketplace, food and beer and wine booths, live entertainment, and ice cream from Softee NorCal. Families can also try a floral vase painting workshop, explore the Outdoor Kitten Lounge, or take part in the Rubber Ducky Scavenger Hunt.

Sunday keeps the summer fun going with carnival rides from 11 a.m.–7 p.m., a craft marketplace, food and beverage booths, live entertainment, and more ice cream. The floral vase painting workshop and Outdoor Kitten Lounge return, while the final Rubber Ducky Scavenger Hunt runs from 10–11:30 a.m. Admission to Summer Days is free, and the event is dog-friendly as long as pups remain leashed. Carnival ride tickets can be purchased in advance or onsite, while the floral painting workshop and kitten lounge have separate fees. Event parking is available for $10 at Parkside Towers and the Century Lot on East Hillsdale Boulevard, with accessible parking at the Foster City Library.

For Bay Meadows residents, Summer Days is another example of how much there is to discover just beyond the neighborhood. With convenient connections throughout San Mateo and the Peninsula, it’s easy to spend the afternoon exploring Foster City’s parks and waterfront before heading home to Bay Meadows for dinner, drinks, or a relaxing evening outdoors. From our own 18 acres of parks and open space to nearby destinations like Leo J. Ryan Park, year round adventures are never far from home.

Visit fostercity.org/summerdays for the complete schedule, event updates, and carnival ticket information.