Set between Lake Elsinore, Temecula, and Menifee, this stretch of Southern California feels like a pocket of open space wedged neatly between growing communities. These low, rugged peaks rise out of the valley almost unexpectedly, creating a small network of trails that offer big views without committing to a full mountain day. It’s the kind of place where you can park, start climbing almost immediately, and still feel removed from the surrounding development.
Some places never lose their magic — no matter how many times you return. Torrey Pines State Natural Reserve is one of those rare spots. Perched above the Pacific in La Jolla, it’s a dramatic mix of rugged cliffs, rare pine trees, and golden beaches that somehow feels wild and refined at the same time.
Some hikes start at trailheads. This one started on a train.
Photo: Coaster Train Along the San Diego Coast
I was up in North County, so my Seven Bridges adventure began on the Coaster, rolling down the coast to Old Town. From there, a quick transfer to the Blue Line trolley took me a couple stops to Middletown. It’s a short but very San Diego walk—palm trees, old homes, and a slow incline—toward the corner of West Laurel and Union.
At 4,973 feet, Black Mesa is the highest point in Oklahoma, ranked #23 among all U.S. state high points and my own #37. Tucked into the far western tip of the Oklahoma panhandle, it sits closer to New Mexico and Colorado than to most of its own state — the kind of place you don’t casually pass through unless you really meant to be there. Luckily, a cross-country drive from San Diego to Nashville created the perfect excuse to finally check it off.
At 13,161 feet, Wheeler Peak is the highest point in New Mexico, ranked #8 among all U.S. state high points and my own #36. I’ve climbed higher mountains before, Kilimanjaro twice and a few peaks in the Alps—but Wheeler is still my highest U.S. high point so far. Even with those bigger summits behind me, I felt this one. On paper, it’s an 8.7-mile round-trip with 2,972 feet of gain, but altitude has a way of making even simple numbers feel different. With an average of 683 feet gained per mile, Wheeler demands a slow, steady kind of grit.
What surprised me most wasn’t the altitude or the trail; it was how mentally challenging this climb became for me.
Mount Marcy, the highest point in New York at 5,344 feet (ranked 21st among U.S. state high points), became my 35th state high point — and one I’ll never forget.
Most of my summit stories begin with sweeping views and triumphant moments. This one began with rain sweeping sideways, fog swallowing the treetops, slick boulders running with water, and wind strong enough to push you off balance. And yet, in its own rugged way, it became one of the most meaningful Adirondack climbs I’ve done on this journey.
Marcy gave us no views.
But it gave us a story that will stay with me forever.
And a group of friends who found their way through all of it together.
In terms of sheer intensity, this climb rivaled — and in some ways exceeded — my experience on Mount Katahdin.
Different mountains, different terrain, but the same reminder: when conditions turn, the margin for error disappears fast.
Let me start by saying this: El Cajon Mountain does not mess around. This isn’t one of those “wow, what a nice stroll through nature” kind of hikes. This is more like “why am I going uphill again?” with a side of “my quads might never forgive me.” And yet — I’d absolutely do it again.
This is an ~11-mile out-and-back with over 3,500 feet of elevation gain, and it earns every bit of its reputation. Short on paper, relentless on the trail — the kind of hike that doesn’t just test your legs, but your patience.
This summer (2025), I’m leading a group to the summit of Mt. Marcy, the tallest peak in New York. At 5,344 feet, it’s a challenging but rewarding hike through the heart of the Adirondacks and a true full-day adventure.
The route covers roughly 14.4 miles round-trip with more than 3,500 feet of elevation gain and typically takes 9–10 hours to complete. It’s not technical, but it is long, demanding, and requires thoughtful preparation—especially when you factor in changing weather, terrain, and fatigue over the course of the day.
Catching up on some hikes from 2024, I found myself at Daley Ranch Park, a 3,201-acre conservation area in Escondido, California. I really didn’t know what to expect. I figured I’d get some miles in, gain a little elevation, and—hopefully—avoid the kind of crowded trails that tend to attract hikers lacking any semblance of trail etiquette. Normally, when I pull into a packed parking lot, my first instinct is to turn around and head somewhere quieter. But I stuck with my plan, and outside of a close encounter with a rattlesnake, Daley Ranch exceeded my expectations.
From one of my favorite songs by Hayley May, John Summit, and Lee Foss:
And there ain’t no city that is quite this pretty
Like summertime in the Chi
As the breeze is blowin’, breathing in this moment
And we ride down Lakeshore Drive
You can’t argue with that—Chicago in the summer is pure magic. If you haven’t experienced it yet, what are you waiting for? During my Upper Midwest adventure this past July, I squeezed in a stop in the Windy City to meet with a couple of potential clients. Spoiler: the trip delivered all the charm, views, and vibes you’d expect from “Summertime Chi.”
Before even getting to Chicago, my trip kicked off with an unexpected highlight at Minneapolis–Saint Paul International Airport: the vibrant art installation 122 Conversations: Person to Person, Art Beyond Borders by Anne Labovitz.
This participatory, kaleidoscopic work celebrates global friendship and connection through art. It’s uplifting, colorful, and a genuinely inspiring way to start a journey—especially one rooted in people, place, and culture.
Photos: 122 Conversations at MSP International Airport
My Chicago digs were none other than the classic Chicago Hilton, perched right on Grant Park. Normally, I’d seek out a boutique hotel. This time, however, Hilton Honors points sealed the deal.
This historic property has hosted royalty, presidents, and rock stars, so I figured it was good enough for me.
Photo: The Chicago Hilton and Towers
One of Chicago’s secret weapons is how easy it is to navigate without a car. My top three ways to get around:
With my first morning free, I laced up my running shoes and set off through Grant Park toward Lake Shore Drive. The lake looked like glass under the early morning sun—an unbeatable way to kick off the day.
Photo: The start of my morning run
I followed the Lakefront Trail north past the marina, already buzzing with boats. Someday, I’ll make it out on the water—but more on that later. Eventually, I veered onto the Chicago Riverwalk, a first for me despite countless visits.
Down here, the city feels different. Skyscrapers loom overhead like guardians, and the pace shifts.
Photos: The Marina | The Chicago River
Along the way, I passed Taco Rio—a taco spot with a prime Riverwalk location that probably makes everything taste better. Right next door, I spotted Urban Kayaks. Could this be my ticket to the water? Mental note made.
Photos: The Riverwalk | Urban Kayaks | Taco Rio Cantina
Photo: Chicago along the Riverwalk
For now, it was time to wrap up the run, grab a quick bite, and head to my first meeting. A strong start to a quintessential Chicago summer day.
Chicago’s food scene isn’t just good—it’s ridiculously, unapologetically epic. Sure, deep-dish pizza gets the spotlight, but the city has range. Michelin stars, vibey neighborhood joints, and creative boundary-pushers all coexist here.
For chefs like me, it’s a place where flavor, culture, and technique collide—sometimes on the same block.
My first stop wasn’t a culinary temple, but it hit exactly where it needed to. Taco Maya’s South Loop location was conveniently around the corner from my hotel
I ordered a trio of tacos: Shrimp, Dorado, and the surprisingly unique Paneer. Bonus points for the salsa bar and complimentary chips. Naturally, I paired it all with a cold Modelo Especial—because tacos without beer are just sad tacos.
Photos: Three’s Company | Chill Vibes and Crispy Chips
Photos: You gotta love a Salsa Bar!
On the Mexican front, Panchos Rooftop and Cantina delivered exactly what I was looking for: rooftop vibes and a solid happy hour. While it checked those boxes, it’s not necessarily a must-hit culinary destination.
Photos: Remember—you’re here for the location, not the food!
Photo: Perfect rooftop day with a view of the Harold Washington Library
For something truly iconic, Lil’ Ba-Ba-Reeba! deserves a spot on your list—especially if you’re a fan of Spanish tapas. I grabbed a seat at the bar and soaked in the lively atmosphere while working through a lineup that reminded me why this place has earned its reputation.
As the younger sibling of Cafe Ba-Ba-Reeba!—and part of the Lettuce Entertain You family—it delivers Spanish small plates that pack big, confident flavors. My picks were exactly what you hope for here: Goat Cheese baked in tomato sauce with house garlic bread, the Roasted Hen of the Woods mushrooms with Manchego cream and chive oil, and, of course, their classic Red Sangria.
Paired together, it’s the kind of bar-top experience that feels effortless, social, and deeply satisfying. Add the sangria, and you’ve got yourself a mini Spanish vacation—no passport required.
Photos: Inside Lil’ Ba-Ba-Reeba! | The Bar
Photos: Baked Goat Cheese | Roasted Hen of the Woods Mushrooms
Over in the uber-cool Logan Square neighborhood, Superkhana International is a creative wonderland of Indian-inspired cuisine. Logan Square itself is a thriving, multicultural hub filled with artsy vibes, trendy cocktail bars, and locally owned shops—worth exploring between bites.
It was a gorgeous night, and I dined on the patio—a perfect setting for this unique and imaginative dining experience. This spot blends creativity and comfort in a way that just works, making it an unmissable culinary gem.
Photos: The Interior | Beautiful night for the Patio
Here’s what I devoured:
Photos: Whipped Paneer | Manchurian Potatoes | Kale Salad
A detour to Little Vietnam led me to Fat Miilk Coffee, one of the main reasons for this Chicago visit. Founded by Lan Ho—whom I met at the National Restaurant Show—this spot is redefining Vietnamese coffee culture.
Their proprietary brewing system allows multiple phins to brew simultaneously while preserving tradition. The result is rich, smooth, deeply satisfying coffee. It’s a must-visit for any coffee enthusiast.
Nearby, Miss Saigon delivered a great lunch. The Shrimp Baos Việt Tacos were crispy, balanced, and held together beautifully—especially with a little Sriracha.
Photos: Fat Miilk Chicago
Photos: Lan Ho | Uber Delish Vietnamese Coffee
Photo: The propriety brewing system with multiple “phins”
While in the area, I grabbed lunch at Miss Saigon and tried their Shrimp Baos Việt Tacos. The fried shrimp were crisp and perfectly seasoned, paired with soft bao that held up well. I made sure to spice it up with some Sriracha, adding a nice kick to the well-balanced flavors and textures.
Photos: I love the banner here! | Cool vibe inside
Photo: Shrimp Baos Việt Tacos
Yes, I ate pizza in Chicago—but not deep-dish. I know, I know… borderline blasphemous in the Windy City. But I’ve always been a bit of a trailblazer, and breaking the rules comes naturally.
Roots Pizza specializes in Quad Cities-style pizza, and it’s a style that deserves more love. The malted dough has a nutty, toasted flavor, rolled thin with a chewy-crisp texture. Toppings go edge-to-edge and are cut into strips rather than wedges. Think of it as a delicious hybrid between deep-dish and New York thin crust.
The atmosphere sealed it. Sitting under the open roof on a warm night, it was perfect al fresco dining and absolutely worth stepping outside the pizza box.
Photos: Dining al Fresco | Quad Cities-style Cheese Pizza
Rounding out my foodie adventure was brunch at avec’s West Loop location, a perennial favorite and a highlight of the trip. I grabbed a seat at the bar—my go-to move at avec—and leaned into bold, Mediterranean flavors.
I went with their Spicy Tomato Shakshuka and the Grilled Shrimp with stone-ground polenta, a pairing that hits every comfort and flavor note. Avec’s commitment to fresh ingredients, confident seasoning, and thoughtful execution makes it a true standout in Chicago’s dining scene.
Photos: I love the inside space at avec!
My menu highlights:
Photos: Spicy Tomato Shakshuka |
Grilled Shrimp with Stone-ground Polenta
Chicago’s culinary scene truly has it all—from comforting taquerias to boundary-pushing fusion spots and everything in between. Whether you’re a foodie hunting hidden gems or a chef looking for inspiration, the Windy City delivers one unforgettable bite at a time.
Chicago’s music scene isn’t just legendary—it’s alive, dynamic, and unapologetically diverse. From blues, jazz, and house to hip-hop and beyond, the city has long been a global music powerhouse.
A century ago, jazz musicians from New Orleans helped transform Chicago into a hub of musical innovation. That tradition of creativity and collaboration still thrives today.
And in summer? It feels like the city itself is singing.
Photo: A mural of BB King, paying tribute to Chicago’s rich musical legacy
Stumbling upon the Square Roots Festival felt like hitting the summer jackpot. Set along Lincoln Avenue, this jam-packed weekend brought together incredible live music, local vendors, family fun, and—let’s be honest—a killer craft beer showcase.
Seriously, it’s the ultimate combo: great tunes, delicious bites, and beer flights that could make any craft lover swoon. Supporting both the Lincoln Square Ravenswood Chamber of Commerce and the Old Town School of Folk Music, it’s a feel-good celebration of Chicago’s cultural heartbeat.
With four stages and three days of music, the lineup blended local favorites with global acts, reflecting the diversity and soul of the city’s music scene.
Photos: The 2024 Line Up | Jammin’ at one of the Stages
Photo: It was a packed house at the Square Roots Festival
I was fortunate to be in Chicago during the Millennium Park Summer Music Series, where Seun Kuti took the stage at the iconic Jay Pritzker Pavilion. The performance was a powerful celebration of Afrobeat’s rich energy and legacy.
As the youngest son of Fela Kuti, Seun has dedicated his career to honoring—and evolving—his father’s musical and political influence. Leading Egypt 80 since his teens, he fuses traditional African rhythms with contemporary themes in a way that’s bold, urgent, and deeply inspiring.
Photos: Jay Pritzker Pavillion | A great opening band played as well!
With albums like From Africa with Fury: Rise and his EP African Dreams, his performances are as much about the message as they are the music. That night felt like a call to action—electrifying, thought-provoking, and unforgettable.
Photos: Seun Kuti and Band
As the concert concluded, the mood shifted fast. Announcers urged the crowd to seek shelter as a rare and powerful storm approached. The July 15, 2024 derecho—accompanied by 32 tornadoes—became the most prolific tornado event in the NWS Chicago forecast area’s history.
Even so, the energy of Seun Kuti’s performance lingered long after the skies opened up.
Photo: This storm was no joke!
Navy Pier turned up the summer vibes with free outdoor concerts, and I caught Almafuerte in action. Led by multi-instrumentalist Jaime Garza, this Chicago-based psychedelic project delivered layered soundscapes and hypnotic rhythms—the perfect soundtrack for a night by the water.
Photos: Navy Pier | A view of Downtown from Navy Pier
Photos: Navy Pier’s Centennial Wheel | Almafuerte
It felt like outdoor music was everywhere, and Sundays on State captured that energy perfectly. Each week, State Street transforms into a pedestrian-only playground filled with live music, art, food trucks, and interactive experiences.
The vibe is lively, relaxed, and deeply communal—a weekly reminder of Chicago’s creative, inclusive spirit.
Photos: Sundays on State
Chicago’s music scene is more than entertainment—it’s an experience. From intimate street performances to grand pavilions, the city’s commitment to live music is undeniable.
When Spain and England clashed in the UEFA Euro 2024 final, I was determined to catch the match with local flavor. After some searching—and a little luck—I landed at Barstool River North.
Packed with jerseys, beers, and collective gasps, it delivered exactly what live sports should: energy, tension, and camaraderie.
Photos: Barstool River North
Photos: Gooooooal!
Later, I made my way to Rossi’s, a true Chicago dive bar legend. From the neon glow to the old-school jukebox, it’s the kind of place that refuses to change—and shouldn’t.
A cold Hamm’s in hand, I soaked in the chatter and dim glow of a bar built on personality and grit, not polish.
Photos: The vibe at Rossi’s
With sunshine leading the way, I also ventured to Federales Logan Square. Tequila lovers, rejoice—this place delivers. From the signature ice shot to finally nailing the bell smash, it was a lively, laughter-filled stop.
No Annie behind the bar that day—but tacos, tequila, and a buzzing patio still made it a win.
Photos: Federales Logan Square
Beneath the urban hustle, there’s another side to the city—the parks. With a robust system of green spaces and city oases, Chicago’s parks aren’t just places to escape the concrete jungle—they’re destinations. Think fountains, gardens, skyline views, and yes, even a mini-golf course (because why not combine nature with a little friendly competition?).
It’s one of the best reminders that Summertime Chi isn’t just about food and music—it’s about space to wander, pause, and look around. Let’s take a stroll through some of the city’s standout parks, where the urban and the green meet in the most beautiful ways.
Known as “Chicago’s front yard,” Grant Park is home to the iconic Buckingham Fountain. It’s the kind of fountain that makes you wish you had a bigger garden—or at least a few more fountains of your own. It’s grand, it’s dramatic, and when it’s lit up at night, you can almost hear Summertime Chi playing softly in the background.
Photo: The iconic Buckingham Fountain
Mini-golf, climbing walls, and an outdoor ice rink in winter—Maggie Daley Park brings the fun. Whether you’re tackling the mini-golf course or scaling the climbing walls like a pro (minus the web-slinging), this park feels like an amusement park for adults who are young at heart.
It’s also a surprisingly great spot for a little friendly competition.
Photo: Maggie Daley Park with Miniature Golf and Climbing Walls
A sleek, modern pedestrian bridge connecting Maggie Daley Park with Millennium Park, the BP Pedestrian Bridge feels like something out of the future. It offers clean lines, thoughtful design, and a solid vantage point for soaking in Chicago’s downtown skyline.
A bridge with style—take that, ordinary walkways.
Photos: BP Pedestrian Bridge
You probably know Millennium Park for Cloud Gate, better known as “The Bean,” but it’s so much more than a photo stop. There’s the Jay Pritzker Pavilion, where you can catch some of the city’s best outdoor concerts, and the breathtaking Lurie Garden, which feels like a secret hideaway tucked away from the surrounding buzz.
Then there’s the Crown Fountain, where you can splash around on a hot day—or simply stand back and enjoy the playful spectacle.
Photo: The “Bean”
Photo: Under the “Bean”
Photos: The Crown Fountain | Lurie Garden
While it might not get the same attention as Chicago’s headline landmarks, the Chicago Exchange Arch is an understated gem in the city’s park system. It blends history, architecture, and just a touch of mystery, making it a rewarding stop if you enjoy discovering places that don’t shout for attention.
Sometimes, it’s the hidden gems that steal the show.
Photo: The Chicago Exchange Arch
From fountains and gardens to golf courses and futuristic bridges, Chicago’s parks are far more than green spaces—they’re an invitation to experience the city from a new angle. Whether you’re wandering past iconic landmarks or stumbling onto quieter corners, it’s clear that Summertime Chi wouldn’t be the same without them.
If you’re looking for a truly unique way to experience Chicago, kayaking along the Chicago River at sunset should be at the very top of your list. The Urban Kayaks Sunset Tour offers a peaceful, two-hour paddle through the heart of the city, with the glow of twilight slowly illuminating some of Chicago’s most iconic buildings.
As you glide along the water, the city rises around you. You get an up-close view of architectural marvels like The MART, the world’s largest commercial building, along with the sleek, modern towers that define Chicago’s skyline. The gentle evening light reflecting off the river adds an almost magical quality, transforming the city’s gritty, industrial backdrop into something serene and unexpectedly beautiful.
Photos: My kayak awaits | The adventure begins!
Photos: The Riverwalk is dotted with waterside cafes | Chicago Marina Towers (right side) – Iconic buildings that appeared in The Bob Newhart Show, Ferris Bueller’s Day Off, The Hunter (where a car drives off the 16th floor of the garage), and The Bear.*
But this isn’t just a leisurely float—it’s an adventure. As you navigate the river, you need to stay alert for larger boats maneuvering through the same waterways. The intersections where the river’s branches meet can be tricky, and keeping an eye out for bigger vessels is part of the experience.
The guides do an excellent job of keeping everyone safe and informed, helping you read the river and anticipate what’s coming next. Still, a little vigilance goes a long way, and that added awareness makes the experience even more engaging.
Photo: Golden Hour on the Chicago River
To reward your efforts, the tour wraps up with a free drink at Taco Rio Cantina next door. It’s the perfect way to kick back, relax, and toast an unforgettable evening on the water.
Whether you’re a kayaking newbie or a seasoned pro, this experience offers a whole new perspective on the city—one that stays with you long after the sun goes down.
Photo: Cheers to a job well done with this celebratory IPA!
My time in Chicago was a reminder of why this city is so special. There’s an ease to it in the summer—a laid-back confidence paired with a vibrant, restless energy. The fusion of cultures, cuisines, and neighborhoods turns the city into an urban playground that delivers on every level.
The pulse of the Square Roots Festival, the mesmerizing sunsets along the Chicago River, and that unmistakable Summertime Chi vibe made it feel like the city was quietly serenading me at every turn. It wasn’t loud or forced—it was just there, woven into the days and nights.
Whether you’re nursing a cold beer in a local dive, running along the lake as the skyline wakes up, or catching live music under an open sky, Chicago in the summer is an experience like no other. It’s a place where music, food, and breathtaking views come together to form a soundtrack you don’t just hear—you live in.
And from here, it was back toward Minneapolis, where my highpointing and state park adventures continued at Timm’s Hill—Wisconsin’s highest point and the next stop on the journey.
Catch you on the road!
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