Where should I stop on my road trip?

Route 1 Itinerary Suggestions

• Temecula

Temecula is the Napa Valley of Southern California and is jam-packed with wineries. Stop at one of these charming spots for a unique wine-tasting experience!

1. Briar Rose Winery: Not only will you experience fantastic wines at Briar Rose, but you’ll also get to experience a piece of Disney history! Built a decade ago by a former Disney employee, the buildings at the winery are replicas of Snow White’s cottage in the 1937 Disney movie. Briar Rose requires a reservation and for all guests to be 21 or over, so plan ahead if you want to experience this quaint spot.
2. Churon Winery: Churon is a little slice of France in Southern California. Offering wine tastings in the chateau-themed boutique hotel, you’ll experience Churon’s finest reds, sweet wines, and dessert wines as you gaze across the Southern California countryside.
3. Doffo: Enjoy Doffo’s Malbec, Zinfandel, Cabernet Sauvignon, Syrah, or its unique red blends, then head to the MotoDoffo museum to see over 200 scooters and motorbikes owned by the proprietor, a lifelong motorcycle enthusiast.

Be sure to stop by Temecula’s Old Town before you go. In Old Town, you’ll feel like you’re in a buzzing 1880s western town with a modern appeal. You’ll find no shortage of restaurants, tasting rooms, boutiques, and antiques on this busy strip of Temecula.

• Riverside

Named for its location beside the Santa Ana River, Riverside is the highest populated city in the Inland Empire region of California.

1. California Citrus State Historic Park: This 248-acre open-air museum celebrates the citrus industry’s impact on the development of Southern California. You’ll feel like you stepped into a vintage postcard as you walk through fields of over 70 varieties of citrus trees, stop for a citrus tasting, and take photos at this charming stop!
2. March Field Air Museum: Airplane fans and military buffs will love this museum with over 70 historic military aircraft on display. Admission is $15 for adults and $6 for children 5-11; children under 4 are free.
3. Van Buren Drive-In: Catch a film in your car sixties style at this historic drive-in theater, or visit before 2 pm any day except Mondays and Fridays to peruse the wares at Van Buren’s eclectic swap meets.
4. Mission Inn Museum: The Mission Inn Museum is a stunning historic inn built in the early 1900s in the mission revival style. Today, this picturesque building is a functioning hotel and museum showcasing local art and history.

• San Bernardino

One of the last big cities you pass through before you get to Big Bear, San Bernardino is the gateway to the San Bernardino National Forest.

1. Original McDonald’s site and museum: Devoted to the golden arches? Stop by to see the original site and free museum to learn how this tiny burger joint became a fast food behemoth.
2. Rim of the World Scenic Byway: Start this route just a short driving distance north of San Bernardino on Hwy 18. This scenic byway welcomes you to the mountains with stunning views along the cliffs of the San Bernardino Mountains and will lead you right into Big Bear. Catch a picturesque sunset on one of the many pull-offs along the route as you make the last leg of your route into Big Bear.

Once you reach Big Bear, you’ll find no shortage of things to do. But if you need inspiration, check out 15 Things to do In Big Bear This January for a list of winter activities or Big Bear’s Best Winter Hiking Trails for hiking recommendations.

Route 2 Itinerary Suggestions

• Torrey Pines

Torrey Pines may be close to home, depending on where you start your trip. This coastal community is well known for its stunning coastal overlooks and beaches.

1.  Torrey Pines State Natural Reserve: Get your legs ready for the car ride by hiking up Torrey Pines’ gorgeous bluffs overlooking the ocean. There are several trail options ranging from under a mile up to just over a mile, each featuring stunning views of the ocean and coastal flora.

• Oceanside/Carlsbad

Oceanside and Carlsbad are two coastal communities with an array of things to do on your drive up to Big Bear!

1. Oceanside Pier: This pier is a hub of activity in Oceanside. Located next to Harbor Beach, the pier draws visitors to stroll, fish, or catch a sunset on its 1,942 ft boardwalk.
2. Legoland California: located in Carlsbad, this Lego-themed park is best for families with kids aged 2-12. The Legoland complex features an aquarium, waterpark, hotel, and theme park with over 60 rides, shows, and attractions.

• San Clemente

A popular tourist destination in Orange County, this stunning coastal city has lots to offer visitors.

1. San Onofre and San Clemente State Beaches: Stop to soak up some sun at either of these two fantastic state beaches. San Onofre State Beach features 3.5 miles of rugged coastline and several well-known surf spots. San Clemente State Beach is closer to town and is well known for its clean facilities, beautiful vistas, and large beach. Both of these iconic beaches have campgrounds that accommodate both tent and RV campers. Be sure to reserve a spot in advance if you plan on spending the night at either beach.
2. Casa Romantica Cultural Center and Gardens: Catch one of the best views of the San Clemente coastline at Casa Romantica. Admission to this historic site includes access to the home’s stunning interior and manicured gardens outside, as well as a small art museum.

• Anaheim

While this route does not take you through Anaheim directly, it takes you close enough to easily make a detour for any number of activities in this city jam-packed with adventure.

1. Disneyland: Need I say more? Experience Disney magic at 2 unique parks and Avengers and Star Wars-themed campuses that’ll make you feel like a kid again.
2. Knott’s Berry Farm: An entire theme park with over 4 areas of rides, shows, and attractions to explore (all themed according to points in California’s history), you’ll find fun for the whole family at Knott’s.
3. Catch a game: Anaheim is home to Angel Stadium, where the LA Angels play, and to the Anaheim Ducks. So between baseball and hockey season, you’ll hopefully be able to catch a home game no matter what time of year you visit.
4. Live Music: Anaheim has its very own House of Blues, a venue frequented by iconic acts. If you plan on spending the night, it’s worth checking out the lineup!

• Riverside

Named for its location beside the Santa Ana River, Riverside is the highest populated city in the Inland Empire region of California.

1. March Field Air Museum: Plane and military buffs will love this museum with over 70 historic military aircraft, including rare operational jets. Admission is $15 for adults and $6 for children 5-11; children under 4 are free.
2. Mission Inn Museum: The Mission Inn Museum is a stunning historic inn built in the early 1900s in the Mission Revival Style. Today, this picturesque building is a functioning hotel and museum showcasing local art and history.

Finish your road trip with a drive up Rim of the World Scenic Byway. This route winds along Hwy 18 and welcomes you into the Big Bear area with stunning overlooks of the San Bernardino Mountains. Catch a picturesque sunset on one of the many pull-offs along the route before you head into Big Bear for your weekend adventure! Once you reach Big Bear, you’ll find no shortage of things to do. But if you need inspiration, check out 15 Things to do In Big Bear This January for a list of winter activities or Big Bear’s Best Winter Hiking Trails for hiking recommendations.

Best time to go on a road trip from San Diego to Big Bear

You’ll find many things to do on a road trip from San Diego to Big Bear year-round, but the trip will vary slightly by season.

Winter and Summer are peak seasons in Big Bear. Big Bear becomes a true wonderland in the winter, drawing many people with its Hallmark Christmas Village-esque allure. Visitors flock to Big Bear’s two ski resorts from December to March to ski and snowboard. Big Bear is beautiful in the winter, however, ice and snow can cause road conditions in the mountains to become dangerous, so any road trip at this time should be made very carefully!

In the summer, visitors beat the heat on Big Bear Lake or hit one of many of Big Bear’s hiking trails. Road conditions are better this season, so you can rest easy driving on Big Bear’s mountain roads. If you want to avoid crowds, head to Big Bear in the Spring or Fall, where you’ll find plenty to do even in the off-season.

Where should I stay in Big Bear?

Sessions Retreat & Hotel is your sanctuary for rejuvenation in Big Bear. Our boutique hotel in Big Bear Lake provides the perfect reprieve from your daily adventures and a place to rest after a long road trip. Far from the hustle and bustle of city life, we offer the perfect opportunity to relax and renew amidst the majestic nature that is Big Bear.

Under new ownership and management, we’re actively working to create a more expansive facility centered around art and wellness, with socially oriented amenities for patrons to foster new connections. While our renovation efforts are underway, our current room selection offers excellent value for your Big Bear getaway, whether traveling alone or with family. Visit us here to learn more about our accommodations perfect for groups of all sizes and trips of all purposes.