Weekend Guide: Things to Do in Santa Cruz & Monterey

We have hit that sweet spot in late August where summer is still in full swing but the pace gets a little easier. Car Week has come and gone, the crowds have thinned, and now it is time to settle into the relaxed golden days that make this part of California so special. This weekend brings the Sand City West End Celebration, Oliver Tree at the Quarry Amphitheater, the Midtown Fridays Block Party, and farmers markets overflowing with the best produce of the year. I have lived in Santa Cruz County for more than 50 years, and late August weekends like this one remind me why I never left.

Every event in this guide I verified through local sources. Let us get into it.

Friday, August 21

Midtown Fridays Summer Block Party

5:00 PM – 8:30 PM | 1111 Soquel Avenue, Santa Cruz
The weekly Midtown Fridays block party is back with live music, rotating food trucks, local vendors, and a family-friendly atmosphere. Free to enter, easy to spend a whole evening wandering, eating, and catching up with neighbors. This is the kind of community event that makes Midtown one of my favorite parts of Santa Cruz. Grab dinner from the food trucks, grab a seat on the lawn, and let the kids run around while you relax.

Death and Saxes at The Crepe Place

5:30 PM – 7:30 PM | The Crepe Place, 1134 Soquel Avenue, Santa Cruz
A free early evening show blending indie rock, folk, and saxophone at one of Santa Cruz's most beloved neighborhood spots. The Crepe Place has that perfect tucked-away patio, great food, and a knack for booking interesting local acts. Free admission. Grab a savory crepe and a beer and settle in for a low-key Friday evening.

Aloha Friday with Ho'omana at Pono Hawaiian Grill

Evening | Pono Hawaiian Grill, 120 Union Street, Santa Cruz
Live Hawaiian music and island vibes at this downtown Santa Cruz favorite. Ho'omana brings traditional and contemporary Hawaiian sounds to Pono's warm, welcoming space. Great food, tropical cocktails, and the kind of aloha spirit that makes you forget the marine layer. No cover.

Whitney at Henry Miller Memorial Library

Evening | Henry Miller Memorial Library, 48603 Highway 1, Big Sur
Indie duo Whitney brings their warm, horn-rich sound to the iconic Henry Miller Library in Big Sur. This intimate outdoor venue tucked into the redwoods is worth the drive alone. Tickets at henrymiller.org. Bring a jacket -- Big Sur cools down fast after sunset.

WoodMill at Discretion Brewing

Evening | Discretion Brewing, 2703 41st Avenue, Soquel
Friday evening live music and excellent craft beer at one of the county's best breweries. WoodMill plays acoustic folk and rock on the spacious Discretion patio. Great for families, dogs welcome, and the beer list is always rotating. A relaxed start to the weekend.

Oliver Tree at Quarry Amphitheater

7:00 PM | Quarry Amphitheater, 1156 High Street, Santa Cruz (UCSC campus)
Oliver Tree brings his genre-bending alt-pop to one of the most beautiful outdoor venues on the Central Coast. The Quarry, carved into the hillside above the Monterey Bay, is an incredible setting for a summer concert. Tickets at ticketmaster.com. If you have never been to a show at the Quarry, this is a great one to start with.

The Charities with Mae Powell and DJ Archive at Moe's Alley

Doors 8:00 PM, Show 9:00 PM | Moe's Alley, 1535 Commercial Way, Santa Cruz
Indie rock and alternative energy at Santa Cruz's premier live music club. The Charities headline with Mae Powell opening and DJ Archive on the decks. Tickets $24.65 at moesalley.com. An intimate venue with great sound.

Rushadicus the Cello Goblin

9:00 AM | SubRosa Community Space, 703 Pacific Avenue, Santa Cruz
A morning show with Rushadicus, the cello-playing goblin of experimental folk music. Yes, it is exactly as wonderfully strange as it sounds. SubRosa is a cozy community space downtown. Free or by donation. A quirky way to start your weekend.

Landing Trio at Albatross Ridge Winery and Kitchen

Evening | Albatross Ridge Winery and Kitchen, Carmel Valley
Friday evening wine and live music in Carmel Valley. Keith Rayburn, Eliza James, and Rick Chelew make up the Landing Trio, playing acoustic originals and covers in the vineyard setting. Great wine, great views, and a relaxed start to the weekend on the Monterey side.

Soapbox Stageworks: Three Summer Comedies

7:00 PM | Monterey History and Art Museum at Stanton Center, 5 Custom House Plaza, Monterey
Original short comedic plays presented by Soapbox Stageworks in the historic Monterey History and Art Museum. Three one-act plays, local talent, and a wonderful addition to Monterey's growing theater scene. Performances Friday and Saturday at 7:00 PM, plus a Sunday matinee. Tickets $25-$35 at soapboxstageworks.com.

Saturday, August 22

Westside Santa Cruz Farmers Market

9:00 AM – 1:00 PM | Mission Street Extension and Western Drive, Santa Cruz
Late August at the Westside market is a thing of beauty. The summer produce is at its absolute peak. Heirloom tomatoes in every shade of red, orange, and purple. Sweet corn, melons, peaches, pluots, basil, sunflowers, and dahlias as big as your head. The Westside market is a Saturday ritual for good reason. Grab a coffee from a local roaster, walk the full loop, and buy way more than you planned.

Scotts Valley Farmers Market

8:00 AM – 12:00 PM | Graham Plaza, 219 Mt. Hermon Road, Scotts Valley
A smaller but mighty market in the heart of the San Lorenzo Valley. Seasonal produce, crafts, and that friendly mountain community feel. A great option if you are starting your day up in the hills.

Aptos Farmers Market at Cabrillo College

8:00 AM – 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, and live bluegrass from the Farmers Market String Band. This market runs year-round and August is one of its best months. Do not skip the fresh-picked berries.

Sand City West End Celebration

11:00 AM – 6:00 PM (Saturday), 11:00 AM – 5:00 PM (Sunday) | Sand City Art Park, 450 Ortiz Avenue, Sand City
This is the weekend's can't-miss event. The West End Celebration is Sand City's annual free outdoor arts and music festival, and it keeps getting better every year. Over 150 artists and vendors, three stages of live music with headliners including Sambada and a full roster of local bands, interactive art installations, dance performances, food vendors, and a community vibe that captures the creative energy of the Monterey Bay. This is a hidden gem that deserves way more attention than it gets. Free to attend. Bring the whole family.

MAH Open Archives

Hours vary | Santa Cruz Museum of Art & History, 705 Front Street, Santa Cruz
The Museum of Art and History opens its Archives Reading Room for visitors to explore Santa Cruz County history. Photographs, documents, maps, and artifacts from the MAH collection. A fascinating way to spend a Saturday morning, especially if you are curious about the history of your own neighborhood.

Afternoon with the Curator at Monterey Museum of Art

Afternoon | Monterey Museum of Art, 559 Pacific Street, Monterey
Join curators Cynthia Wagner Weick and Joaquin Turner for an afternoon exploring current exhibitions at the Monterey Museum of Art. A wonderful deep dive into the art and history of the Monterey Peninsula. Museum admission applies. Check montereyart.org for exact timing.

Jade in Watercolor Class

10:00 AM – 1:00 PM | Pacific Grove Museum of Natural History, 165 Forest Avenue, Pacific Grove
A hands-on watercolor workshop at the PG Museum, focusing on painting jade plants and succulents. All skill levels welcome. Materials included. A relaxing creative morning on the Monterey Peninsula. Tickets at pgmuseum.org.

Paradise PG: An Afternoon of Tropical Splendor

3:00 PM | Pacific Grove Community Center, 515 Junipero Avenue, Pacific Grove
A tropical-themed afternoon in Pacific Grove with live music, food, and community fun. A great way to spend a Saturday afternoon on the Peninsula. Free or by donation.

Controlled Chaos Improv at California's First Theatre

Evening | California's First Theatre, Scott and Pacific Streets, Monterey
Improv comedy in the oldest theater in California. Controlled Chaos brings their quick-witted, audience-driven improv to this historic venue for a night of laughs. A unique Monterey experience.

Live Music at Lucy's on Lighthouse

2:00 PM – 4:00 PM | Lucy's on Lighthouse, 555 Lighthouse Avenue, Pacific Grove
The Next Blues Band plays Saturday afternoon at Lucy's on Lighthouse. A cozy neighborhood spot with great food and live music on the patio. Free to enjoy while you eat and drink.

Earthless with Primitive Ring at Moe's Alley

Doors 8:00 PM, Show 9:00 PM | Moe's Alley, 1535 Commercial Way, Santa Cruz
Instrumental psychedelic rock from San Diego's Earthless. Long jams, heavy riffs, and a light show that will take you somewhere else. Primitive Ring opens. Tickets $36.95 at moesalley.com. Earplugs recommended. This will be loud and beautiful.

Sun Kil Moon at Golden State Theatre

8:00 PM | Golden State Theatre, 417 Alvarado Street, Monterey
Sun Kil Moon brings their intimate, storytelling-driven indie folk to the beautifully restored Golden State Theatre in downtown Monterey. Mark Kozelek's quiet, evocative songwriting fills the historic hall with a warmth that suits the venue perfectly. Tickets at goldenstatetheatre.com. A Saturday night for the contemplative music lovers among us.

Sunday, August 23

Live Oak / Eastside Farmers Market

9:00 AM – 1:00 PM | 15th Avenue and East Cliff Drive, Santa Cruz
Sunday is farmers market day on the east side. A smaller, neighborhood-friendly market with local produce, artisan vendors, and a relaxed pace. Grab your market finds and walk a block to the coastal trail or Seabright Beach for a Sunday morning picnic.

Sand City West End Celebration – Day 2

11:00 AM – 5:00 PM | Sand City Art Park, 450 Ortiz Avenue, Sand City
A second full day of art, live music, and community celebration at this free festival. If you missed Saturday, Sunday is your last chance. The art park setting is beautiful in the late-summer light and the music lineup on Sunday is just as strong as Saturday.

The Music Never Stopped: A Celebration of the Grateful Dead with Nice Device

Afternoon | Shearwater Tavern, 267 Bonifacio Place, Sand City
Sunday afternoon Dead vibes at Shearwater Tavern right in Sand City. Nice Device plays Grateful Dead covers and deep cuts. Great food, cold beer, and a perfect way to extend your West End Celebration weekend. No cover.

Soapbox Stageworks – Final Performance

Afternoon matinee | Monterey History and Art Museum at Stanton Center, 5 Custom House Plaza, Monterey
The final performance of Soapbox Stageworks' Summer Comedies. One last chance to catch these original one-act plays in the historic museum setting. An affordable, fun arts outing on the Monterey Peninsula.

Mighty Mike Schermer and Friends – 60th Birthday Celebration

3:00 PM | Moe's Alley, 1535 Commercial Way, Santa Cruz
Blues guitar legend Mighty Mike Schermer celebrates his 60th birthday with an afternoon show at Moe's Alley. A master of the blues guitar with deep Santa Cruz roots, this will be a special set with plenty of guest players. Tickets $28.80 at moesalley.com. A Sunday afternoon full of soulful licks and good vibes.

Big Blue Community Indigo Vat at SubRosa

12:30 PM | SubRosa Community Space, 703 Pacific Avenue, Santa Cruz
A hands-on community indigo dye workshop in downtown Santa Cruz. Bring something white and take home something blue. SubRosa is a welcoming creative space that hosts these community dye vats regularly. Free or by donation. A meditative, hands-on way to spend a Sunday afternoon.

Hunny Pot at Discretion Brewing

3:00 PM | Discretion Brewing, 2703 41st Avenue, Soquel
Sunday afternoon live music and craft beer at the Soquel brewery. Hunny Pot brings an eclectic mix of folk, rock, and Americana to the patio. A fitting way to close out a long weekend. Family-friendly, dog-friendly, rain or shine.

All Weekend: Outdoor Adventures

Kayaking Elkhorn Slough

Daily | Moss Landing (about 20 minutes south of Santa Cruz)
Elkhorn Slough in late summer is teeming with wildlife. Sea otters drifting through 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 tours. The slough is calm and protected, perfect for beginners. Early morning is the best time to see the otters at their most active.

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 days. In August the creeks are low, so bring water.

Surfing at Cowell's Beach

Daily | Cowell's Beach, Santa Cruz (just west of the Wharf)
August has the warmest water temperatures of the year. Cowell's is the classic beginner break with gentle waves, sandy bottom, and plenty of surf schools. Club Ed, Adventure Out, and Surf School Santa Cruz all offer lessons with gear included. If you have never surfed, this is the weekend to try.

Monterey Bay Aquarium

Open daily, 10:00 AM – 5:00 PM (Sat-Sun 9:00 AM – 5:00 PM) | 886 Cannery Row, Monterey
A world-class attraction right in our backyard. The Kelp Forest, Open Sea exhibit with tuna and sea turtles, the touch pools, and the always-mesmerizing jellyfish gallery. With Car Week crowds behind us, this is a great weekend to visit without the crush. Book ahead online to guarantee entry.

Biking the Monterey Bay Coastal Recreation Trail

18 miles from Castroville to Pacific Grove
One of the most scenic paved trails in California, running along the old railroad line between Castroville, Marina, Seaside, Monterey, and Pacific Grove. Flat and easy. Rent a bike from Bay Bikes on Alvarado Street and ride the section between Monterey and Pacific Grove for ocean views, Cannery Row, and the Pacific Grove waterfront.

Santa Cruz Beach Boardwalk

Open daily with extended summer hours | 400 Beach Street, Santa Cruz
The Boardwalk is in full summer mode. 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. Fewer crowds than during Car Week means shorter lines.

Whale Watching

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

Food & Drink Highlights

Sand City West End Celebration Food Vendors

The Sand City festival brings a curated selection of food trucks and vendors. Expect local favorites, festival classics, and creative bites. The beer and wine garden keeps things cool. Pair your lunch with live music and art browsing.

Abbott Square Market

725 Front Street, Santa Cruz
Our downtown food hall on the edge of Abbott Square. Luna's Boriken Bites serves excellent Puerto Rican dishes. India Gourmet has a permanent kiosk serving their famous farmers market favorites seven days a week. Multiple other vendors and a full bar. The outdoor plaza is perfect for warm August evenings.

Albatross Ridge Winery and Kitchen

Carmel Valley
Friday evening live music with the Landing Trio, plus estate wines and a full kitchen. The views over Carmel Valley are hard to beat. A wonderful Friday evening option on the Monterey side.

Lucy's on Lighthouse

555 Lighthouse Avenue, Pacific Grove
Live music Saturday and Sunday afternoons at this Pacific Grove neighborhood spot. Great food, warm atmosphere, and a cozy patio. Saturday: Next Blues Band. Sunday: Meez. Free music with your meal.

Shearwater Tavern

267 Bonifacio Place, Sand City
Sunday afternoon Grateful Dead tribute with Nice Device at this Sand City gastropub. Right around the corner from the West End Celebration. Good food, cold beer, and Dead vibes to close out the weekend.

Notable Community News

West End Celebration Returns to Sand City. This free, family-friendly arts and music festival is one of the Monterey Bay's best-kept secrets. Over 150 artists and vendors, three stages of live music, interactive art installations, and a creative community atmosphere that captures the spirit of Sand City's art district. If you have never been, this is the weekend to discover it. Free parking, free admission, all ages.

Oliver Tree at the Quarry. Friday night's concert at UCSC's Quarry Amphitheater is one of the biggest shows of the late summer at this iconic venue. The Quarry has been hosting world-class performances since the 1960s, and the hillside amphitheater with its views over the Monterey Bay is one of the most beautiful concert settings anywhere.

Midtown Fridays Winding Down. The weekly Midtown Fridays Summer Block Party has been a highlight of the season. With summer ending soon, each remaining Friday is a chance to experience this community-driven event. Food trucks, live music, local vendors, and the best neighborhood energy in Santa Cruz.

Summer Produce at Peak. This is the moment to stock up on everything the Central Coast grows best. Heirloom tomatoes, peaches, pluots, sweet corn, melons, basil, sunflowers, and dahlias. The farmers markets this weekend (Westside Saturday, Live Oak Sunday, Aptos Saturday, Scotts Valley Saturday) are all overflowing with the best of the season. Buy extra. You will thank yourself mid-week.

Shareable Social Captions

Planning to post about your weekend? Here are some ready-to-copy captions for Instagram and Facebook. I write these the way I share my own weekend plans with friends.

Sand City West End Celebration is this weekend and it is free. Over 150 artists, three stages of live music, art installations, and that creative community energy that makes the Monterey Bay special. I am going Saturday with the whole family. Who is coming with me? 🎨 🎶 #SantaCruzEvents #ThingsToDoSantaCruz #WeekendInSantaCruz #WestEndCelebration #MontereyBay

Late August in Santa Cruz is the sweet spot. The farmers markets are overflowing with heirloom tomatoes and peaches, the Quarry Amphitheater has Oliver Tree on Friday, Midtown Fridays is still going, and the redwood trails are quiet after Car Week. This is the weekend to get out and soak it all in. 🌾 🌊 #SantaCruzLife #WeekendInSantaCruz #SantaCruzEvents #ThingsToDoSantaCruz #CaliforniaSummer

My Saturday plan: Start at the Westside Farmers Market for sunflowers and heirloom tomatoes, head down to Sand City for the West End Celebration (free art and live music all day), then Earthless at Moe's Alley for a psychedelic rock nightcap. Sunday: Live Oak market and a beach walk. A perfect August weekend. 🌺 🎸 #SantaCruzEvents #WeekendInSantaCruz #ThingsToDoSantaCruz #SantaCruzLife #MontereyBay

Free outdoor art festival with 150+ vendors. The West End Celebration in Sand City runs Saturday and Sunday with live music on three stages, art installations, food vendors, and zero admission. This is one of those events that reminds you why the Central Coast creative community is so special. Bring the kids, bring a blanket, come hungry. ✨ 🎨 #WestEndCelebration #SantaCruzEvents #ThingsToDoSantaCruz #WeekendInSantaCruz #MontereyBay

Friday night at the Quarry. Oliver Tree at the Quarry Amphitheater is the show to catch this weekend. One of the most beautiful outdoor venues on the Central Coast, carved into the hillside above the bay. Plus Midtown Fridays Block Party if you want something more low-key. Two great options for Friday night. 🎵 ☀️ #SantaCruzEvents #WeekendInSantaCruz #ThingsToDoSantaCruz #QuarryAmphitheater #SantaCruzLife

Sunday is for blues and blue dye. Mighty Mike Schermer's 60th birthday show at Moe's Alley at 3 PM, then the Big Blue Community Indigo Vat at SubRosa at 12:30 PM. How is that for a perfect Santa Cruz Sunday? Blues guitar and hands-on indigo dyeing in the same afternoon. Only in this town. 🎸 🧹 #SantaCruzEvents #WeekendInSantaCruz #ThingsToDoSantaCruz #SantaCruzLife #LiveMusic

Enjoy the weekend, everyone. Whether you are browsing art at the West End Celebration, catching Oliver Tree at the Quarry, filling your bags at the farmers market, or just finding a quiet spot on the beach with a good book, I hope this weekend gives you exactly what you need. This community is special, and weekends like this one remind me why I have spent the last 50-plus years here and never wanted to be anywhere else. If you are thinking about buying or selling a home in Santa Cruz or Monterey County, or if you have questions about the market in your neighborhood, 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

Weekend Guide: Things to Do in Santa Cruz & Monterey, August 21-23