Weekend Guide: Things to Do in Santa Cruz & Monterey, September 4-7, 2026

This is the last long weekend of summer, and both counties are sending it off in style. The Monterey County Fair returns with a rodeo, carnival rides, fair food and live entertainment. Roaring Camp Railroads has train rides, live music, and a Moonlight Dinner Party under the redwoods. The Capitola Beach Festival is coming up later in the month and I have all the details. And if you have been meaning to hit the farmers markets, catch live music, or just soak up the last of the golden-hour beach days, this is the weekend to do it.

I have lived in Santa Cruz County for more than 50 years, and Labor Day weekend has always felt like the grand finale of summer. There is a bittersweet energy to it. The days are still long and warm, but you know the foggy mornings and shorter afternoons are right around the corner. That is exactly why this weekend matters. Make it count. Here is your guide.

Thursday, September 3 -- The Fair Opens

Monterey County Fair -- Opening Day

11:00 AM to 11:00 PM | Monterey County Fair & Event Center, 2004 Fairground Road, Monterey
The Monterey County Fair kicks off Thursday with the theme "Cowboy Boots & Coastal Roots." This is Seniors Day, so anyone 62+ gets in free. Carnival rides, livestock exhibits, competitive displays, fair food classics, and free live entertainment included with admission. The fair runs through Monday, so you have five days to experience it all. Pre-sale tickets available online. Parking is $25 at Monterey Pines Golf Course with a free shuttle. Children 5 and under are free every day.

Friday, September 4

Monterey County Fair -- Military and Veterans Day

11:00 AM to 11:00 PM | Monterey County Fair & Event Center, 2004 Fairground Road, Monterey
Friday at the fair is Military and Veterans Day, with free admission for active duty military, veterans, and their dependents. The Short Track Motorcycle Race runs from 5:00 to 7:00 PM, and the carnival is in full swing. Fair food, live music, and all the county fair energy you can handle. A great Friday night outing for the whole family.

The Sam Chase & The Untraditional at Moe's Alley

Doors 8:00 PM, Show 9:00 PM | Moe's Alley, 1535 Commercial Way, Santa Cruz
Kick off your Labor Day weekend with roots rock and Americana from San Francisco's The Sam Chase & The Untraditional. Their live show is high-energy, heartfelt, and the perfect way to start a long weekend of celebration. Thanks Buddy opens. Tickets at moesalley.com.

Santa Cruz Beach Boardwalk -- Extended Summer Hours

Open daily, rides until approximately 10:00 PM | 400 Beach Street, Santa Cruz
The Boardwalk is in full summer mode through Labor Day with all rides, games, arcades, and attractions open daily. The Giant Dipper, Logger's Revenge flume ride, mini golf, laser tag, and the historic 1911 Looff Carousel are all running. Summer evenings on the Boardwalk with the lights reflecting on the sand never get old. This is the last weekend for daily summer operations before the schedule shifts to weekends only.

Watsonville Wednesday Market

2:00 PM to 7:00 PM | Watsonville Plaza, 358 Main Street, Watsonville
Early September is peak harvest season in the Pajaro Valley. The Watsonville market is where you find the best berries, stone fruit, and seasonal produce south of Santa Cruz. A great stop on your way down to the Monterey County Fair.

Saturday, September 5

Westside Santa Cruz Farmers Market

9:00 AM to 1:00 PM | Corner of Highway 1 and Western Drive, Santa Cruz
Early September at the Westside market is special. The late-summer produce is still abundant, and the early fall crops are starting to appear. Heirloom tomatoes, sweet corn, peppers, eggplants, basil, sunflowers, and the first of the autumn squash. The market is fully organic-certified with live music and that community atmosphere that makes it a Saturday ritual. Grab a coffee, walk the full loop, and stock up for the long weekend.

Aptos Farmers Market at Cabrillo College

8:00 AM to 12:00 PM | 6500 Soquel Drive, Aptos
Voted "America's Favorite Farmers Market in California" three years running. Over 90 vendors offering certified organic produce, artisan cheeses, pastured meats, fresh pasta, olive oils, and the Farmers Market String Band playing bluegrass. The Aptos market is a destination in its own right. Worth the trip from anywhere in the county.

Scotts Valley Farmers Market

8:00 AM to 12:00 PM | 219 Mt. Hermon Road / Graham Plaza, Scotts Valley
A friendly, smaller market with local produce, crafts, and a warm mountain community feel. Perfect if you are starting your weekend in the San Lorenzo Valley.

Del Monte Center Farmers Market

8:00 AM to 12:00 PM | Del Monte Shopping Center, 1410 Del Monte Center, Monterey
Over 60 vendors at this lively Saturday market. Local produce, artisan foods, and a sunny lot with mountain views. If you are heading to the Monterey County Fair later in the day, this is a perfect morning stop on the Peninsula.

Monterey County Fair -- Flying U Rodeo Night

Fair open 11:00 AM to 11:00 PM, Rodeo at 6:30 PM | Monterey County Fair & Event Center, 2004 Fairground Road, Monterey
Saturday night at the fair means rodeo. The Flying U Rodeo brings bull riding, barrel racing, and all the Western action you expect from a county fair rodeo. The rodeo runs from 6:30 to 7:30 PM and is included with fair admission. Arrive early for good seats. The carnival, exhibits, and fair food are open all day.

Roaring Camp Railroads -- Steam Train Rides

9:30 AM to 5:00 PM | 5401 Graham Hill Road, Felton
Roaring Camp offers two classic train experiences through the Santa Cruz Mountains. The Redwood Forest Steam Train climbs through towering old-growth redwoods to the summit of Bear Mountain on a narrow-gauge railway. The Santa Cruz Beach Train connects Roaring Camp to the Santa Cruz Beach Boardwalk through six miles of redwood forest. Both run daily through the holiday weekend. Live music from Steve Bennett performs in the Town of Roaring Camp. A perfect family adventure that combines history, nature, and old-fashioned fun.

Clinton Fearon & Boogie Brown Band at Moe's Alley

Doors 8:00 PM, Show 9:00 PM | Moe's Alley, 1535 Commercial Way, Santa Cruz
Reggae legend Clinton Fearon, a founding member of The Gladiators, brings his Boogie Brown Band to Moe's Alley for a night of roots reggae, soul, and Jamaican rhythms. Clinton's voice and songwriting have been shaping reggae music for over five decades. Kava Jah & The Remedy open. Tickets at moesalley.com.

Old Monterey Marketplace

4:00 PM to 8:00 PM | Alvarado Street, Monterey
The Tuesday Old Monterey Marketplace moves to a special Saturday Labor Day edition this week. This farmers market on Alvarado Street features local produce, artisan foods, live music, and a festive downtown atmosphere. A great way to spend a Saturday evening in Monterey before the fair fireworks.

Sunday, September 6

Live Oak / Eastside Farmers Market

9:00 AM to 1:00 PM | 15th Avenue and East Cliff Drive, Santa Cruz
Sunday is farmers market day on the east side. A neighborhood-friendly market with local produce, artisan vendors, and a relaxed morning pace. Grab your market haul and walk a block to Seabright Beach for a Labor Day weekend picnic with the waves rolling in.

Del Monte Center Farmers Market

8:00 AM to 12:00 PM | Del Monte Shopping Center, 1410 Del Monte Center, Monterey
The Sunday Del Monte market returns with over 60 vendors. This is one of the largest and most popular markets on the Monterey Peninsula. Local produce, artisan breads, flowers, and specialty foods in the rear parking lot.

Monterey County Fair -- Fiesta del Charro

Fair open 11:00 AM to 11:00 PM, Performances at 3:00 PM and 6:30 PM | Monterey County Fair & Event Center, 2004 Fairground Road, Monterey
Sunday at the fair features Fiesta del Charro, a Mexican rodeo and cultural celebration with thrilling equestrian performances, traditional music, and vibrant costumes. Two performances at 3:00 PM and 6:30 PM. Included with fair admission. This is one of the most exciting and colorful events of the entire fair.

Roaring Camp Railroads -- Moonlight Dinner Party

Evening | 5401 Graham Hill Road, Felton
A special Sunday evening event at Roaring Camp. Enjoy a BBQ dinner followed by a leisurely moonlit steam train ride through the redwoods. Live music, a campfire, and line dancing round out the evening. Reservations required. This is a magical experience that sells out every year. Check roaringcamp.com for tickets and details.

Tommy Castro & The Painkillers at Moe's Alley

Doors 3:00 PM, Show 4:00 PM | Moe's Alley, 1535 Commercial Way, Santa Cruz
Blues legend Tommy Castro and his band The Painkillers bring their award-winning brand of electric blues, soul, and rock to Moe's Alley for a Sunday afternoon show. Castro is a multiple Blues Music Award winner and his live performances are electrifying. An early show means you can enjoy world-class blues and still have your evening free. Tickets at moesalley.com.

El Mercado Popular de Watsonville

8:00 AM to 4:00 PM | Santa Cruz County Fairgrounds, 2601 East Lake Avenue, Watsonville
One of the largest outdoor markets in the region, El Mercado Popular features approximately 200 vendors selling fresh produce, traditional foods, clothing, crafts, and household goods. The energy is vibrant, the prices are fair, and the produce is exceptional. A true south-county tradition.

Monday, September 7 -- Labor Day

Monterey County Fair -- Final Day

10:00 AM to 11:00 PM | Monterey County Fair & Event Center, 2004 Fairground Road, Monterey
The fair's final day. Monday hours start earlier at 10:00 AM. All the exhibits, carnival rides, and fair food are available for one last day. If you have not made it to the fair yet, this is your last chance. The fairgrounds close at 11:00 PM, so you can enjoy a full day of family fun.

Roaring Camp Railroads -- Labor Day

9:30 AM to 5:00 PM | 5401 Graham Hill Road, Felton
The final day of Roaring Camp's special Labor Day weekend programming. Both the Redwood Forest Steam Train and the Santa Cruz Beach Train are running. Live music and family activities continue in the Town of Roaring Camp. The Beach Train continues running through September 27, and the Redwood Forest Train runs through October 31, so this is not your last chance, but it is the last day of the holiday celebration.

Santa Cruz Beach Boardwalk -- Last Day of Summer Daily Operations

Rides open approximately 11:00 AM to 10:00 PM | 400 Beach Street, Santa Cruz
Labor Day marks the end of the Boardwalk's daily summer schedule. After today, the rides switch to weekends only through October. The Boardwalk Bowl Summer Fun Pass is valid through today. September 7 is also the last day for extended summer hours. If you have been waiting for the perfect day to ride the Giant Dipper one more time, this is it.

Pacific Grove Certified Farmers Market

3:00 PM to 7:00 PM | Central Avenue and Grand Avenue, Pacific Grove
Monday afternoon farmers market in Pacific Grove. Summer hours run through September, so this is one of the last Monday markets of the season. Local produce, artisan foods, and a charming small-town setting. A lovely way to spend a Labor Day afternoon on the Peninsula.

Coming Up: Mark Your Calendar

Capitola Beach Festival -- September 26-27

Capitola Village
The new Capitola Beach Festival is the successor to the beloved Begonia Festival (which ended in 2017). This year's theme is "Toy Takeover" and it looks like a blast. Saturday features the Little Wharf 3-Miler Fun Run, a Sand Sculpture Contest, Cornhole on the Beach, Children's Art activities, a Scavenger Hunt, live music on the beach, and a Lighted Nautical Parade on Soquel Creek followed by a Drone Show. Sunday has a Fishing Derby, Rowboat Races, and a Horseshoe Tournament. Free and family-friendly. I will have a full guide for this weekend closer to the date.

Capitola Art & Wine Festival -- September 12-13

Capitola Village
The 43rd annual Capitola Art & Wine Festival features over 100 juried fine artists, pours from Santa Cruz Mountains wineries, live music on the Esplanade bandstand, and food vendors. Free admission. Wine tasting requires a Festival Glass and tasting tokens (must be 21+). One of the most scenic art festivals on the Central Coast.

Santa Cruz County Fair -- September 16-20

Santa Cruz County Fairgrounds, 2601 East Lake Avenue, Watsonville
The 2026 Santa Cruz County Fair theme is "Apple Pies and Starry Skies." Agricultural exhibits, livestock shows, live entertainment, animal displays, carnival rides, and family activities. A classic county fair experience in the heart of the Pajaro Valley.

All Weekend: Outdoor Adventures

Kayaking Elkhorn Slough

Daily | Moss Landing (about 20 minutes south of Santa Cruz)
Early September is still prime time on the slough. Sea otters floating among the eelgrass, harbor seals hauled out on the mudflats, egrets and herons stalking the shallows. Kayak Connection and Blue Water Ventures both offer rentals and guided naturalist tours. Calm, protected waters perfect for beginners. Bring a camera and sunscreen.

Surfing at Cowell's Beach

Daily | Cowell's Beach, Santa Cruz (just west of the Wharf)
September has some of the warmest water temperatures of the year. Cowell's is the classic beginner break: gentle waves, a sandy bottom, and plenty of surf schools ready to help you catch your first wave. Club Ed, Adventure Out, and Surf School Santa Cruz all offer lessons with gear included. This is the last weekend of peak summer conditions.

Hiking the Redwoods

Daily | Henry Cowell Redwoods State Park, Felton; Fall Creek Unit, Felton; The Forest of Nisene Marks, Aptos
Three incredible redwood parks within 15 minutes of each other. Henry Cowell has the easy 0.8-mile old-growth loop. Fall Creek offers quieter, creekside trails through second-growth forest. Nisene Marks has 30-plus miles of trails from flat fire roads to steep climbs. All are shaded and cool even on warm September days. The creeks are running low this time of year, so bring extra water.

Monterey Bay Coastal Recreation Trail

18 miles from Castroville to Pacific Grove
One of the most scenic paved trails on the California coast. Walk, run, or bike along the bay with views of Cannery Row, the Monterey Peninsula, and on clear days, the entire curve of the bay. Rent a bike from Bay Bikes on Alvarado Street and ride the section between Monterey and Pacific Grove. The trail is less crowded after the summer rush, making September an ideal time to explore it.

Monterey Bay Aquarium

Open daily, 10:00 AM to 5:00 PM | 886 Cannery Row, Monterey
A world-class attraction in our backyard. The Kelp Forest, the Open Sea exhibit with tuna and sea turtles, the touch pools, and the mesmerizing jellyfish gallery. September brings thinner crowds compared to peak summer. Book ahead online to guarantee entry. A perfect family activity for a warm afternoon.

Whale Watching in Monterey Bay

Daily departures | Fisherman's Wharf, Monterey, and Santa Cruz Harbor
Humpback whales are still actively feeding in Monterey Bay through early fall. Half-day tours depart from both Monterey's Fisherman's Wharf and the Santa Cruz Harbor. Blue Ocean Whale Watch and Princess Monterey Whale Watching offer daily trips. Bring a warm jacket. The ocean is cool even on warm September days, and the whales are spectacular right now.

Santa Cruz Beach Boardwalk

Open daily through Labor Day | 400 Beach Street, Santa Cruz
The Boardwalk is closing out its summer daily schedule. After Labor Day, the park shifts to weekends only through October. This is your last chance for weekday rides, extended evening hours, and the full summer experience until next Memorial Day. The Giant Dipper at sunset is still one of the best views on the Central Coast.

Food & Drink Highlights

Monterey County Fair Food

Let us be honest: fair food is half the reason to go. Corn dogs, funnel cakes, turkey legs, kettle corn, cotton candy, and every fried food on a stick you can imagine. The fair runs through Monday, so you have plenty of opportunities to indulge. Do not skip the livestock barn either. The 4-H and FFA kids work all year on their animals and they love talking about them.

Roaring Camp BBQ & Moonlight Dinner

The Moonlight Dinner Party on Sunday evening includes a BBQ dinner served in the historic Town of Roaring Camp. After dinner, you board a steam train for a moonlit ride through the redwoods. Campfire, live music, and line dancing follow. It is a one-of-a-kind dining experience in the Santa Cruz Mountains.

Abbott Square Market

118 Cooper Street, Downtown Santa Cruz
Open all weekend. Grab arepas, wood-fired pizza, poke bowls, Puerto Rican dishes from Luna's Boriken Bites, and India Gourmet's famous farmers market favorites. The outdoor plaza is perfect for a casual dinner on a warm September evening.

Westside Santa Cruz Wine Tasting

The Westside wine trail is minutes from the farmers market. Birichino Winery (204 Church Street), Storrs Winery (303 Potrero Street), and MJA Vineyards (328 Ingalls Street) all have tasting rooms open Saturday. Bottle Jack Winery and Silver Mountain Vineyards are right next door. A perfect afternoon pairing with your market haul.

Alvarado Street Brewery

426 Alvarado Street, Monterey
A Monterey institution. Alvarado Street Brewery's taproom on Alvarado Street serves excellent craft beer and pub food in a lively downtown setting. A great spot to refuel between the farmers market and the fair. Their IPAs and stouts are consistently among the best on the Central Coast.

Notable Community News

Monterey County Fair Returns September 3-7. Five days of carnival rides, rodeo action, Fiesta del Charro, livestock exhibits, free live entertainment, and all the fair food you can handle. Thursday is Seniors Day (62+ free), Friday is Military and Veterans Day (free admission), and children 5 and under are free every day. The Flying U Rodeo is Saturday night, and Fiesta del Charro is Sunday. This is the fair's 2026 edition with the theme "Cowboy Boots & Coastal Roots."

Roaring Camp Labor Day Weekend. Steam train rides through the redwoods, live music, family activities, and the Moonlight Dinner Party on Sunday evening. Both the Redwood Forest Steam Train and the Santa Cruz Beach Train are running. The Beach Train continues through September 27 and the Redwood Forest Train through October 31, so you have more chances if this weekend does not work.

Capitola Beach Festival Announced for September 26-27. The successor to the historic Begonia Festival returns with a "Toy Takeover" theme. Sand sculpture contest, lighted nautical parade, drone show, rowboat races, and more. Free and family-friendly. I will have a full guide for this event as it gets closer.

Last Weekend for Summer Daily Boardwalk Operations. After Labor Day, the Santa Cruz Beach Boardwalk switches to weekends only. This is your final chance for weekday rides and extended evening hours until next summer. The Boardwalk Bowl Summer Fun Pass is valid through September 7.

Santa Cruz County Fair Coming September 16-20. "Apple Pies and Starry Skies" is the theme for the 2026 Santa Cruz County Fair at the fairgrounds in Watsonville. Agricultural exhibits, livestock shows, carnival rides, and family fun. Mark your calendar.

Capitola Art & Wine Festival on September 12-13. Over 100 artists, Santa Cruz Mountains wines, live music, and food in beautiful Capitola Village. Free admission. A wonderful way to spend a late-summer weekend.

Shareable Social Captions

Planning to post about your weekend? Here are some ready-to-copy captions for Instagram and Facebook, written as if I am sharing my own weekend plans with friends.

Last long weekend of summer, and we are going out with a bang. The Monterey County Fair is on with a rodeo, carnival rides, and fair food. Roaring Camp has steam trains through the redwoods. The Boardwalk is running daily for the last time until next summer. And the farmers markets are still overflowing with late-summer produce. See you out there. 🎪 🚂 #SantaCruzEvents #ThingsToDoSantaCruz #WeekendInSantaCruz #MontereyCountyFair #LaborDayWeekend

My Labor Day weekend plan: Saturday morning at the Westside Farmers Market for the last of the summer peaches. Then the Monterey County Fair for the Flying U Rodeo. Sunday: Roaring Camp Moonlight Dinner Party under the redwoods. Monday: one last ride on the Giant Dipper before the Boardwalk switches to weekends. Who is joining me? 🌴 🚘 #SantaCruzEvents #ThingsToDoSantaCruz #WeekendInSantaCruz #SantaCruzLife #CaliforniaSummer

Family-friendly Labor Day alert. The Monterey County Fair has something for every age: carnival rides, animals, fair food, and free live entertainment. Plus Roaring Camp's steam trains through the redwoods, and the Boardwalk in full summer mode. Pack the crew and make some memories. 👨‍👩‍👧‍👦 🎪 #FamilyFunSantaCruz #SantaCruzEvents #WeekendInSantaCruz #MontereyCountyFair #LaborDayWeekend

Last call for summer. After this weekend, the Boardwalk goes weekends only. The farmers markets start shifting toward fall. The sunsets come a little earlier. But right now, right this weekend, summer is still here in full force. Corn dogs at the fair, sea otters at Elkhorn Slough, blues at Moe's Alley, and the Giant Dipper lit up against the night sky. Go get it. 🌊 🌙 #SantaCruzEvents #WeekendInSantaCruz #ThingsToDoSantaCruz #SantaCruzLife #MontereyBay

Already planning ahead. The Capitola Beach Festival is September 26-27 with a sand sculpture contest, drone show, and lighted nautical parade. The Capitola Art & Wine Festival is September 12-13. And the Santa Cruz County Fair is September 16-20. Summer may be winding down, but September in Santa Cruz is packed. Stay tuned for full guides on all of them. 🎨 🍷 #SantaCruzEvents #ThingsToDoSantaCruz #WeekendInSantaCruz #Capitola #SantaCruzCountyFair

Enjoy the long weekend, everyone. Whether you are riding the Giant Dipper one last time, watching the rodeo at the Monterey County Fair, or taking a moonlit steam train through the redwoods, I hope this Labor Day weekend gives you exactly what you need. If you are thinking about buying or selling a home in Santa Cruz or Monterey County, or if you have questions about what this market looks like for your situation, I would love to hear from you. Call me at (831) 247-5719 or visit the contact page. I want you to make informed decisions, and I love helping people find their place in this beautiful corner of California.

Talk soon.
Kieron Bery, REALTOR® with Century 21 Masters