Winter doesn’t have to slow down your sense of adventure. As a professional pet caregiver, I’ve seen how much joy comes from traveling with your dog and making memories together. From our home base in Alexandria and Arlington, there are so many dog friendly vacations just a short drive away. Winter even makes some of these spots feel a little more magical.

Why Winter Travel With Your Dog Is Worth It

Traveling with your dog in the colder months feels calmer and more peaceful. Crowds shrink, rates drop, and you get more space to explore at your own pace. Many hotels and rentals offer excellent off-season deals and are thrilled to welcome pets this time of year.

Picture quiet beaches, scenic overlooks, cozy mountain towns, and wide-open trails without the usual noise of peak season. With a little planning, your dog can thrive on winter adventures and enjoy the fresh air, new scents, and shared time with you.

Planning a Dog Friendly Vacation

A good winter trip starts with choosing a destination that truly welcomes pets. Look for places with dog-friendly trails, walkable main streets, and lodging that makes pets feel at home.

Check listings for pet-friendly hotels, cabins, and vacation rentals. Many offer thoughtful touches like dog beds, fenced outdoor spaces, and easy access to parks or trails. Before you book, read the property’s pet policy to avoid surprises.

Once you’ve picked a destination, plan a few simple outings. Winter walks through historic towns, scenic overlooks along the mountains, quiet beaches, or a visit to a local dog park make the trip feel complete. Pack your dog’s essentials—food, bowls, leash, waste bags, meds, and a cozy blanket—to help them settle in.

The Best Dog-Friendly Towns for Winter Trips (Short Drive Edition)

Some nearby towns come alive in winter and make perfect weekend getaways for you and your pup.

Charlottesville, VA

Just a couple of hours from Alexandria and Arlington, Charlottesville offers dog-friendly breweries, outdoor patios, walkable streets, and scenic mountain views. You can explore the historic pedestrian mall, visit vineyards that allow dogs outside, and wander through open spaces that stay beautiful year-round.

Frederick, MD

Frederick’s charming downtown, riverfront paths, and dog-friendly shops create an easygoing winter atmosphere. Many restaurants with covered outdoor seating welcome dogs, even in colder months.

St. Michaels, MD (Eastern Shore)

This waterfront town is peaceful in winter. You can stroll the harbor, visit small shops, and enjoy quiet walks by the water with your pup.

Dog-Friendly Beaches Worth the Drive

Winter is one of the best times for a quiet beach day with your dog. Many beaches lift seasonal restrictions and allow dogs on-leash—and sometimes off-leash—during the colder months.

Assateague Island, MD/VA

Wide-open shoreline, beautiful dunes, and plenty of space to play. Dogs are allowed on the Maryland side year-round.

Virginia Beach (North End)

Off-season rules are relaxed, which makes it perfect for long walks with your pup along the ocean.

If you’re up for a longer road trip, the South Carolina coast offers miles of dog-friendly shoreline, especially in winter. Just check local rules to confirm leash requirements.

Top Dog-Friendly Hiking Trails for Winter Adventures

Local trails are breathtaking this time of year. The crisp air, bare trees, and quiet atmosphere make it a great season for hiking with your dog.

Shenandoah National Park

Only certain trails allow dogs, but the ones that do offer beautiful winter views. Skyline Drive is also stunning when the air is cold and clear.

Mason Neck State Park (VA)

The Bay View Trail is flat, scenic, and perfect for dogs of all ages. With water views, wildlife sightings, and quiet paths, it’s an easy half-day adventure.

Great Falls Park (VA/MD)

While dogs must stay leashed, the winter scenery along the Potomac River is hard to beat.

Pet-Friendly Accommodations That Feel Like Home

Finding the right place to stay makes all the difference. Look for cabins, cottages, and small inns that openly welcome dogs.

Many properties near Shenandoah, Charlottesville, and the Eastern Shore offer:

• Pet welcome kits
• Outdoor seating areas
• Fenced yards
• Trails right outside your door

Think about what your dog enjoys most. Playful pups may love a rental with a yard, while older or more relaxed dogs may prefer a quiet hotel room near walking trails.

Dog-Friendly Restaurants and Breweries

You don’t have to skip good food just because you’re traveling with a dog. Many places in Virginia and Maryland offer covered outdoor seating or heated patios that stay pet friendly all winter.

Breweries, cideries, and wineries—especially around Charlottesville, Richmond, and the Shenandoah region—are known for welcoming dogs. It’s an easy, relaxing way to enjoy local flavors with your pup curled up beside you.

Dog Parks and Outdoor Play Spots

Give your dog a chance to burn off winter energy by visiting local dog parks during your trip. Many towns have fenced parks with big play areas and space to run. It’s a great way for your dog to stretch their legs after time in the car and meet new friends.

Dream-Worthy Destinations for Future Trips

Even if you stay close to home this winter, it’s always fun to look ahead and imagine where your next pet friendly vacation might take you. Dog owners have so many fantastic destinations to choose from, especially if you’re dreaming about places filled with natural beauty, dog friendly activities, and welcoming atmospheres built for pets and people alike.

If you love mountain adventures, picture yourself driving the scenic stretches of the Blue Ridge Parkway or wandering through the peaceful mountains of West Virginia. Many of these areas offer numerous dog friendly trails where your four legged friend can enjoy crisp air, open space, and quiet moments in nature. These spots rank among the best dog friendly vacations because they’re laid-back, beautiful, and full of pet friendly vacation spots that make traveling dogs feel right at home.

Beach lovers can dream about future trips to the Outer Banks, the Oregon Coast, or the pristine beaches along Lake Michigan. The coastal charm of Orange County and the pristine beaches of Northern California are also favorites for dog owners. Places like Carmel Beach and Lake Tahoe have been absolutely loved by pet parents for years thanks to their relaxed “pets allowed” rules, wide-open space, and abundance of dog friendly spots. Many beaches along both coasts welcome leashed dogs year-round, creating the perfect setting for long walks, quiet mornings, and sandy paws.

If you’re craving a blend of nature and city life, destinations like San Francisco and its iconic Golden Gate Bridge offer memorable moments for you and your furry companion. The nearby Columbia River Gorge in the Pacific Northwest is another bucket-list area with dramatic views and incredible scenic trails that are just as enjoyable for dogs as they are for humans. Wine lovers can even plan future wine tasting weekends at dog friendly wineries that offer outdoor tables, fire pits, and dog friendly outdoor seating where everyone—two-legged and four-legged—can unwind together.

For pet parents who want a mix of charm and walkability, a classic college town can be a fantastic destination. Many small towns built around universities offer dog friendly accommodations, cozy restaurants with a covered patio, and pet amenities that make your stay feel easy and relaxed. These pet friendly spots often include shops and small parks designed to be enjoyed by dogs alike, giving you plenty to explore at your own pace.

Nature lovers can also dream ahead to visiting iconic locations like Acadia National Park, where the rugged coastline and crisp forest paths deliver the perfect blend of outdoor adventures and breathtaking views. Whether you’re dreaming about the lakes of the Midwest, the coastal cliffs of the West Coast, or the forests of New England, there’s no shortage of dog friendly vacation spots waiting to be discovered.

No matter where your future adventures take you—dog friendly hotels in charming towns, cozy cabins tucked near outdoor attractions, or scenic getaways with dog friendly accommodations—there’s a perfect place for you and your fur baby. Let these daydreams fuel your inspiration as you plan your next pet friendly vacation with your loyal four legged companion by your side.

Tips to Make Winter Travel With Your Dog Easier

A little planning goes a long way:

• Pack warm layers for you and your dog.
• Bring your dog’s food, bowls, leash, treats, and a comfy blanket.
• Check pet policies before arriving.
• Keep your dog leashed on unfamiliar trails.
• Protect their paws in cold weather.

How Kate’s K9 Pet Care Helps You Travel Stress-Free

Travel isn’t always a fit for every pet, and that’s okay. When your dog is happiest at home, you can still travel with peace of mind knowing they’re in loving hands.

At Kate’s K9 Pet Care, we provide personalized visits, dog walks, overnight stays, pet taxi services, and even supply delivery. We’re licensed, bonded, and insured, and we send updates and photos after every visit so you can truly relax while you’re away.

Whether you’re taking a quick winter getaway or planning something longer, we make sure your pets stay happy, safe, and cared for.

Your next adventure is calling. Go explore—and let us take care of the rest.