Best Neighborhoods for Calm, Structured Dog Walking in Annapolis

Mike and Colleen Bass

Nov 7, 2025

Pack Walking

A dog walking on a quiet street in West Annapolis, showcasing a calm environment ideal for structured leash training.

Discover the charm of Annapolis while enhancing your dog's walking experience with our top picks for calm and structured routes! From tree-lined streets to quiet sections of popular trails, this guide will help you and your pup enjoy safer, more enjoyable walks together.

Discover the charm of Annapolis while enhancing your dog's walking experience with our top picks for calm and structured routes! From tree-lined streets to quiet sections of popular trails, this guide will help you and your pup enjoy safer, more enjoyable walks together.

Annapolis is full of charm—and full of dogs. But when it comes to behavior-focused walking, not every street, park, or trail is created equal.

At Pup Scouts, we walk dogs across the greater Annapolis area in routes designed to reinforce calm, regulated leash behavior—not reactivity or overstimulation. Whether your pup is in a private dog walk or a pack dog walk, the where of the walk matters just as much as the how.

Here are some of our top neighborhood picks for structured walking in Annapolis.

🏡 1. Homewood + West Annapolis

These two adjacent neighborhoods offer:

  • Low traffic side streets

  • Sidewalks with minimal foot/bike congestion

  • Tree-lined shade for comfort

  • Predictable walking loops for route repetition

💡 Ideal for: leash skill building, reactivity recovery, and reliable routine.

🏞️ 2. Quiet Sections of the B&A Trail (Near Poplar Trail)

The busiest trailheads on the B&A can be chaotic—but the lesser-used Poplar Trail connector section offers:

  • A narrow but walkable stretch

  • Limited distractions mid-day

  • Great visual exposure without high intensity

💡 Best used for: pack dog walks, exposure walks for sensitive dogs, and recovery after structured dog training.

🌲 3. Bay Ridge Side Streets (Avoid the Main Stretch)

The residential zones of Bay Ridge (away from the waterfront chaos) offer:

  • Predictable walking routes

  • Plenty of visual variety without overload

  • Light dog traffic during 11am–2pm windows

💡 Tip: Stay west of Bay Ridge Avenue for best walking consistency.

🏘️ 4. Murray Hill (Midday Only)

While this area gets busy during mornings and evenings, midday walking offers a great balance of:

  • Shade

  • Curbs for training work

  • Controlled sidewalk patterns

💡 Use for: experienced pack dogs or private walkers working on “neutrality in public.”

⛵️ 5. Eastport (Near Back Creek)

Parts of Eastport are high-traffic—but the streets near Back Creek Park are quieter and offer solid repetition opportunities with moderate sensory input.

💡 Ideal for dogs who need to generalize leash skills beyond their neighborhood.

What Makes These Routes Ideal?

At Pup Scouts, we choose routes based on:

✅ Predictability (same sidewalks = less scanning)

✅ Exposure without chaos

✅ Safe pacing and minimal interruption

✅ Leash-training reinforcement opportunities

We avoid:

🚫 Busy downtown corners

🚫 Dog park entrances

🚫 Unpredictable waterfront congestion

🚫 Routes with high dog or foot traffic during peak hours

Want Structured Walks in Your Part of Annapolis?

We currently serve:

📍 West Annapolis Dog Walking

📍 Eastport Dog Walking

📍 Murray Hill Dog Walking

📍 Arnold Dog Walking and surrounding areas

Wondering if we are walk in your location? Check here or give us a quick call!

🎯 Book your consultation or observation walk today

Good walks start with smart routes!

What services are you interested in?

Pick as many as you’d like. We'll create a care plan that fits your routine.

Let’s get to know you and your pup.

Within a day, you'll hear from your dedicated local team to tailor your pup’s care and get you on the schedule.

Let’s get to know you and your pup.

Within a day, you'll hear from your dedicated local team to tailor your pup’s care and get you on the schedule.

Let’s get to know you and your pup.

Within a day, you'll hear from your dedicated local team to tailor your pup’s care and get you on the schedule.

What services are you interested in?

Pick as many as you’d like. We'll create a care plan that fits your routine.

Let’s get to know you and your pup.

Within a day, you'll hear from your dedicated local team to tailor your pup’s care and get you on the schedule.

Let’s get to know you and your pup.

Within a day, you'll hear from your dedicated local team to tailor your pup’s care and get you on the schedule.

Let’s get to know you and your pup.

Within a day, you'll hear from your dedicated local team to tailor your pup’s care and get you on the schedule.

What services are you interested in?

Pick as many as you’d like. We'll create a care plan that fits your routine.

Let’s get to know you and your pup.

Within a day, you'll hear from your dedicated local team to tailor your pup’s care and get you on the schedule.

Let’s get to know you and your pup.

Within a day, you'll hear from your dedicated local team to tailor your pup’s care and get you on the schedule.

Let’s get to know you and your pup.

Within a day, you'll hear from your dedicated local team to tailor your pup’s care and get you on the schedule.

What services are you interested in?

Pick as many as you’d like. We'll create a care plan that fits your routine.

Let’s get to know you and your pup.

Within a day, you'll hear from your dedicated local team to tailor your pup’s care and get you on the schedule.

Let’s get to know you and your pup.

Within a day, you'll hear from your dedicated local team to tailor your pup’s care and get you on the schedule.

Let’s get to know you and your pup.

Within a day, you'll hear from your dedicated local team to tailor your pup’s care and get you on the schedule.

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