Best Dog-Friendly Winter Activities: The Ultimate Annapolis Guide
Mike and Colleen Bass
Mar 25, 2025
Local Guides
Hey there, fellow dog parent! As someone who’s spent countless winters exploring Annapolis with my four-legged friends, I know firsthand how challenging it can be to keep your pup entertained during the chilly months. But don’t worry – I’ve got some fantastic ideas that’ll have your furry friend wagging their tail all winter long! Whether you’re new to the area or a longtime resident, these dog friendly winter activities will help you and your pup make the most of the season!
Braving the Cold: Safety First!

Before heading out for dog friendly winter activities, remember these essential tips:
Check those paw pads regularly for ice buildup or salt irritation
Invest in proper winter gear (yes, some dogs really need it!)
Keep walks shorter during extreme cold
Watch for signs of discomfort like shivering or lifting paws
Consider booties for paw protection against salt and ice
Always bring water to prevent dehydration
Monitor your dog’s energy levels and behavior
Check the weather forecast before planning outdoor activities
The amazing team at MD Pup Scouts recommends limiting outdoor time when temperatures drop below 32°F for small or short-haired breeds. For larger, thick-coated breeds, they can typically handle temperatures down to 20°F, but always use your best judgment!
Local Winter Activities Your Pup Will Love
When the weather cooperates, Annapolis offers some pawsome winter activities:
Historic District walks (bonus: fewer tourists in winter!)
Sandy Point State Park beach romps
Downtown window shopping (many stores are dog-friendly!)
Naval Academy Bridge walks for the adventurous
City Dock explorations during quieter winter days
Quiet Creek Trail adventures on mild winter days
Jonas Green Park visits for scenic water views
Pro tip: The MD Pup Scouts blog regularly updates with seasonal activities and safety tips specific to our area!
Indoor Enrichment Ideas

Don’t let winter blues affect your pup! Here are some indoor activities to keep them mentally stimulated:
Hide-and-seek with treats
Puzzle toys filled with their favorite snacks
Indoor obstacle courses using household items
Training sessions (perfect time to learn new tricks!)
Nose work games with hidden treats
Tug-of-war with appropriate toys
Indoor fetch in a cleared space
Interactive toy play sessions
Food-dispensing ball games
Making the Most of Winter Walks
When you do venture out, try these tips to make walks more enjoyable:
Choose protected routes with less wind exposure
Walk during the warmest part of the day (usually early afternoon)
Bring water (yes, even in winter!)
Keep moving to stay warm
Dress appropriately – both you and your pup
Stick to well-maintained paths to avoid hidden ice
Consider reflective gear for early morning or evening walks
Plan shorter, more frequent walks instead of long ones
Avoid walking on roads treated with salt when possible
Post-Adventure Care

After your winter activities, don’t forget these important steps:
Wipe down paws to remove any salt or ice
Check between toe pads for snow buildup
Remove wet gear immediately
Offer fresh water
Provide a warm, cozy spot to rest
Monitor for any signs of cold-related stress
Give extra cuddles and praise for being a good sport!
Brush out any snow or ice balls from their fur
Check for any redness or irritation on paw pads
Winter in Annapolis doesn’t have to mean endless days of boredom for your furry friend. With these activities and safety tips in mind, you can make this season just as exciting as any other! And if you ever need professional help keeping your pup active and engaged, the experienced team at MD Pup Scouts is always here to help with their comprehensive winter services and expert guidance.
Stay warm and wag on, Annapolis pet parents! 🐾❄️
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