Memorial Day weekend marks the unofficial start of summer on the Monterey Peninsula, and 2026 is shaping up to be one of the best weekends of the year to visit. With California Roots returning to the Fairgrounds, the free MST Trolley back on the road, humpbacks rolling through the Bay, and wildflowers still going strong along the coast, there is no shortage of ways to fill three (or four) sun-soaked days. Here is your guide to making the most of your Memorial Day weekend in Monterey County.
Catch California Roots Music & Arts Festival
The Memorial Day weekend headliner, Cali Roots, returns to the Monterey County Fair & Event Center from Friday, May 22, through Sunday, May 24, 2026. The 2026 lineup is one of the strongest in the festival’s history, with Ice Cube, Rebelution, Soja and Tash Sultana headlining. Expect good vibes, food and beverage vendors, art installations and the festival’s trademark commitment to sustainability.
Honor the Day at the Free Memorial Day Concert
On Memorial Day itself, Monday, May 25, pack a blanket and head to the Colton Hall lawn in downtown Monterey for the Monterey County Pops! free Memorial Day concert. The full 40-piece orchestra performs a patriotic program of marches, popular favorites and tributes to those who served. The lawn opens around 10 a.m. for the rehearsal; the concert traditionally kicks off in the early afternoon. Bring chairs, a picnic and the whole family. Admission is free.
Go Glamping at The Camp at Carmel Valley
Trade traffic for tree canopy at The Camp at Carmel Valley, a 115-acre retreat tucked into the rolling hills 20 minutes inland from the coast. Tented cabins come stocked with real beds and linens, and the on-site activity menu includes archery, swimming, tennis, pickleball, yoga and miles of hiking, turning the long weekend into a proper escape. Breakfast is also included with the three-night minimum, which lines up perfectly with the Friday-to-Monday holiday.
Hop On the Free MST Trolley
Memorial Day weekend marks the seasonal return of the free MST Trolley, which loops every 10–15 minutes between downtown Monterey, Old Fisherman’s Wharf, Cannery Row and the Monterey Bay Aquarium, daily from 10 a.m. to 6 p.m. through Labor Day. Park once and let the trolley do the rest. It is the easiest way to skip the holiday weekend traffic and the search for parking on Cannery Row.
Hit the Beach
Monterey County’s 99 miles of coastline mean a beach for every kind of holiday. Pack a volleyball for Del Monte Beach, surf the breaks at Asilomar, post up with a picnic at Lovers Point in Pacific Grove, watch the sea otters play at the kelp-lined coves of Point Lobos, or chase the sunset down to Carmel River State Beach. For something wilder, head south on Highway 1 to Garrapata or Pfeiffer Beach, where the purple-sand pockets and arches feel like a world away.
Go Whale Watching
Memorial Day lands in the heart of humpback season on Monterey Bay, with blue whales, orcas and massive pods of common dolphins regularly making appearances. Multiple whale watching tour operators depart daily from Old Fisherman’s Wharf, and most run morning and afternoon trips of about three hours. Mornings tend to be calmer and clearer; afternoons often deliver the most active feeding. Either way, dress warmer than you think you need to.
Cruise the 17-Mile Drive
If you only have a couple of hours, the 17-Mile Drive is still the most cinematic introduction to the Peninsula. Cruise past the Lone Cypress, Bird Rock and Spanish Bay, then turn the gate fee into a meal; the $12.50 admission is reimbursed with a $35+ purchase at any Pebble Beach Resorts restaurant (excluding Pebble Beach Market). The Bench, Stillwater Bar & Grill and The Tap Room are all classics. Reservations are smart on a holiday weekend.
Hike the Coast & Catch the Last of the Wildflowers
Late May is prime hiking weather. Coastal fog usually burns off by mid-morning, and the wildflower bloom is still putting on a show. Follow the coastline and walk the Monterey Bay Coastal Recreation Trail along the bay, or head inland to Garland Ranch in Carmel Valley for sweeping valley views. For a guided option, Big Sur Guides and Hiking lead guests of many abilities through the Big Sur wilderness.
Sip Local: Breweries, Wineries & Tasting Rooms
Monterey County’s craft scene is firing on all cylinders. On the beer side, hit up Alvarado Street Brewery & Grill and Peter B’s Brewpub in downtown Monterey, Dust Bowl Brewing on your way to Old Fisherman’s Wharf, The Brass Tap in Marina, Hops & Fog in Pacific Grove, and Other Brother Beer in Seaside. For wine, the tasting rooms of Carmel-by-the-Sea put a dozen Carmel Valley and Santa Lucia Highlands producers within easy walking distance. Make sure to visit Caraccioli Cellars, Wrath Wines and VIN by the Sea for unique and elevated wine experiences. Want a bigger day out? Head up Carmel Valley Road for vineyard-side tastings at Folktale Winery, Bernardus Vineyards and Winery, Holman Ranch Tasting Room and Cowgirl Winery.
Travel Responsibly
We love sharing this place, and we’d like to keep it this way for the next visitor. Stay on designated trails, give wildlife the space they need (especially harbor seals with pups in late May), pack out everything you pack in, and use the recycling and compost bins where you find them. Take the trolley, share a ride or walk between neighborhoods when you can. Small choices add up across a holiday weekend.
Plan Your Stay
Memorial Day weekend books up early in Monterey County. Lock in where to stay, then start mapping out your weekend. Browse Monterey County hotels and inns or see the full event calendar to plan around what is happening while you are here.
