The Perfect 48 Hour Itinerary: Winter in Denver
Two days. One city. Endless moments to savor. With The Rally Hotel as your home base in the heart of downtown Denver, this 48-hour itinerary blends cozy comforts, city adventures, and the kind of experiences that make every trip feel like a story worth telling.
Why Winter Is the Best Time to Visit Denver
Winter in Denver brings its own magic: fewer crowds, cozy dining culture, and easy access to the mountains just outside the city. Denver’s clear, sunny winter days make exploring downtown a pleasure, while seasonal activities like ice skating at McGregor Square and starry hot tub nights offer unique winter experiences. Whether you’re craving snowy adventures or warm, inviting indoor escapes, Denver in winter delivers.
Day 1: Downtown Delights & Rooftop Views
Morning: Wake Up & Fuel Up
Start your day at The Original, where brunch is anything but ordinary. Reimagined classics and fun seasonal or monthly specials turn breakfast into a little adventure of its own. From clever spins on Eggs Benedict to hearty favorites with a twist, there’s always something new to try. Pair it with a bold cup of coffee or a playful brunch cocktail and you’re ready to take on the day.
Midday: Sip, Stop, & Explore
Step outside The Rally Hotel and let downtown Denver guide your afternoon. Winter at McGregor Square has a rhythm all its own. Lace up your skates at McGregor Skate, peek at a movie or the game on the big screen, grab a quick bite at Milepost Zero, or browse Chained Up Permanent Jewelry for a fun keepsake. Whether you skate, snack, or simply wander, there’s something new around every corner.
Then wander over to Dairy Block, a downtown hidden gem full of boutique shops, cozy cafés, and local art worth lingering over. For a sweet local treat, head to Little Man Ice Cream in LoHi (Lower Highlands). You can take scenic 30-minute walk along Platte Street through Commons Park, crossing the Platte River with gorgeous city and river views, or opt for a quick 5-minute drive.
By the time you finish this loop, you’ll have tasted, seen, and discovered a little of everything!
Afternoon: Art, History, & Downtown Culture
After a lively midday, let the heart of Denver guide you to a slower, curious pace. Start at Union Station, where history meets everyday city life. From there, a short walk brings you to the Museum of Contemporary Art Denver. Rally Hotel guests can enjoy $3 off general admission, an exclusive perk for those staying on property.
If shopping calls, explore The Vintage Label for curated, one-of-a-kind pieces, then check out Rockmount Ranch Wear, a Denver institution known for its iconic western wear and heritage craftsmanship. By weaving together history, art, and a touch of local flavor, this afternoon offers a taste of Denver that’s as enriching as it is effortlessly charming.
Evening: Firelight & City Nights
As the sun sets, take in the Denver skyline from the Skybridge Rooftop Deck & Plunge Pool at The Rally Hotel, where fire pits, a heated plunge pool, and a hot tub create a cozy winter evening.
Later, step into Call Me Pearl, located in The Rally Hotel, for handcrafted drinks and delightful bites that are both playful and sophisticated. If you’re in the mood to keep exploring, take a short walk to the Cruise Room, one of Denver’s most historic cocktail lounges, known for its classic vibes and timeless charm. This hidden gem is full of character and a touch of old-school Denver flair. It’s the perfect way to end your first day in the city.
Day 2: Mountain Majesties & Neighborhood Charm
Morning/Midday: Hit the Slopes or the Streets
The mountains are calling! Denver’s just a short drive from world-class ski areas, making it the perfect base for a day on the slopes. From Copper Mountain (about 75 miles, roughly 1 hour 30 minutes) to Winter Park (about 67 miles, roughly 1 hour 20 minutes) and Breckenridge (around 80 miles, roughly 1 hour 40 minutes), there are runs for every skill level—or if you’re not skiing, enjoy a scenic drive with crisp winter air and breathtaking mountain views.
Exclusive to Rally Hotel guests: take advantage of the Mountain Majesties package, offering 20% off stays for local ski pass holders throughout the 2025/2026 season. Need gear? Rentals and equipment are available at most ski areas, or swing by Christy Sports to pick up everything you need before heading up. For a smooth trip, the Colorado Department of Transportation website is a handy resource to check road and traffic conditions.
Not headed to the slopes? Denver’s neighborhoods are full of discovery. RiNo Art District is a feast for the senses—colorful murals, cozy coffee shops, and quirky boutiques make wandering a delight. Winter mornings here are bright and peaceful, with little surprises around every corner waiting to be discovered.
Afternoon: Lunch & City Strolls
Coming down from the slopes:
After a morning in the mountains, The Original is the perfect spot to refuel. Hearty classics and seasonal specials provide just the right mix of comfort and flavor to recharge before an afternoon of exploring downtown.
Staying in the city:
If you’ve been wandering downtown or exploring RiNo, swing by Cart-Driver for fresh, creative pizzas in a lively, colorful space—a relaxed stop to grab a bite before continuing your afternoon adventures.
From either starting point, a stroll through Larimer Square is a must. As Denver’s first historic commercial district, it’s lined with beautifully restored Victorian‑era buildings and a lively mix of shops, eateries, and boutiques that reward casual wandering. Whether you’re grabbing a coffee and browsing local goods, peeking in at seasonal décor, or simply soaking up the festive string lights overhead, Larimer Square blends historic charm with modern energy in a way that feels uniquely Denver.
Evening: Dinner, Drinks, & Cozy Moments
After a full day of winter adventures, return to The Rally Hotel where the evening is yours to savor. Maybe it’s slipping into your hotel robe, ordering room service, and enjoying a cozy dinner in bed while a movie plays—after a day on the slopes, there’s nothing better.
If you’re looking to keep the night lively, Carmine’s is a nearby favorite for couples or families, and Rally Hotel guests enjoy a complimentary first glass of wine. For drinks with a little sparkle, Call Me Pearl or La Loma offers a perfect nightcap just steps from your room. No matter how you choose to end the day, whether tucked in for quiet comfort or out discovering more of Denver’s evening charm, the city lights, crisp winter air, and cozy comforts of The Rally Hotel make it a trip to remember.
A Stay to Remember
Denver has a way of giving you exactly what you’re looking for—whether that’s adventure, rest, connection, or a bit of all three. And with The Rally Hotel as your home base, every moment becomes just a little more comfortable, a little more memorable, and entirely your own.
FAQs For Your Winter Denver Weekend
Is Denver worth visiting in winter?
Absolutely! Fewer crowds, sunny winter days, cozy dining, seasonal activations, and easy access to the mountains make it an ideal winter destination.
Where should I stay for a winter weekend in Denver?
Downtown Denver hotels like The Rally Hotel put you steps from McGregor Square, Union Station, Larimer Square, RiNo, and some of the city’s best winter experiences.
How close is Denver to ski resorts?
Within 1–1.5 hours, you can reach Copper Mountain, Winter Park, Breckenridge, and more—perfect for a day trip or a winter getaway.
What can you do in downtown Denver in winter?
Skate at McGregor Square, sip cocktails at rooftop bars, explore art districts and historic streets, and enjoy cozy local dining—all easily walkable from The Rally Hotel.