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Dog-Friendly Fall Activities Around Annapolis, Maryland

The leaves and temperatures are dropping, and it officially feels like fall in Maryland. Take advantage of these beautiful, crisp days… and don’t let your dog miss out on the fun! There are so many dog-friendly fall activities to enjoy around Annapolis and Anne Arundel County, and we did the work to put them all in one place for you. From pumpkin patches, to arts festivals, to pup parades – there’s never been a better time to be a dog owner (or dog!) in Maryland. Check out all of the amazing dog-friendly fall activities below, and don’t forget to tag us @MDPupScouts in your pictures from each event!



10/14  |  10AM-3PM: Fall Fun Day at Kinder Farm Park 

Have fun with hayrides, farm animals, arts and crafts, sawmill demos, a pumpkin patch, food, and more! Gate fees are waived the day of the event.

10/14 – 10/15  |  10AM-4PM: Art @ The Park at Quiet Waters Park 

This annual arts festival located in the magnificent setting of Quiet Waters Park features original artwork from numerous exhibitors, both local and from around the country. It includes musical performances, art demonstrations, activities, and specialty food. Dogs are welcome at all outside venues, but are not allowed in the buildings. Gate fees apply.

10/15  |  12AM-3PM: Fall Fest at Annapolis Town Center 

Enjoy all things fall, including pick your own pumpkin patch, a hay maze, games and crafts, face painting, costume contest, live music, food trucks, and more! The first 600 kids will receive a free gift with a donation of canned goods to the Anne Arundel County Food Bank! Tickets are free and required.

10/21  |  2PM-9PM: Fall Fest on West 

Enjoy live music, pumpkins, kids’ events, outdoor dining and more on West Street in Historic Annapolis followed up with Dinner Under the Stars from 5-9pm with live music. Don’t miss the Annapolis Corgi Club Parade at 2:30! The Fall Fest is free to attend.

10/22  |  10AM-5PM: Maryland Avenue and State Circle Fall Festival 

This free street festival features arts, crafts, antiques, home decor, live music, food trucks, children’s activities and much more! Come in Costume for the Halloween Pup Stroll!



11/4 – 11/5  |  10AM-6PM: MD Corn Maze Dog Friendly Weekend, hosted by MD Pup Scouts

Get lost with your pup in an 8-Acre Superhero Corn Maze, then stay & play on the farm all day! Go on a hayride, climb a giant straw pyramid, climb tire mountain, grab something yummy from Carnival Eats, and more. Use code MDPS23 when purchasing your tickets and 15% of your ticket price will be donated to the Anne Arundel County SPCA.

11/5  |  11AM-5PM: West Street First Sunday Arts Festival

For the final First Sunday Arts Festival of the season, enjoy shopping along beautiful West Street in downtown historic Annapolis. Shop with over 100 vendors, enjoy live entertainment, and grab a bite to eat from one of West Street’s delicious restaurants. The Festival is free to attend.

11/12  |  9:30AM: Community Park Walk with MD Pup Scouts

Join MD Pup Scouts pack leaders and other Annapolis-area dog owners for a walk together through Quiet Waters Park. We’ll meet at 9AM in Lot N for refreshments and introductions, and begin walking at 9:30AM. The daily entrance fee for Quiet Waters Park is $6/vehicle.


All Season

Councell Farms Pumpkin Patch and Field of Fun 7 days/week until 10/31  |  9:30AM – 5:30PM

With 20+ farm related activities, including the corn maze, jumping pillow, combine slide and pumpkin patch, there’s something for everyone at Councell Farms’ Field of Fun. Tickets are required.

Montpelier Farms Hours vary through November

Spend your day at the farm enjoying a 7-acre corn maze, rope maze, hay rides, animals, pedal karts, giant hill slides, pumpkin bowling, and more! Tickets are required.


MD Pup Scouts: Your Seasonal Solution for Dog Walking Services 

Maintaining a year-round dog walking routine can be challenging, especially if you have a busy schedule. This is where MD Pup Scouts comes into play as your go-to solution for professional dog walking services. We understand the importance of keeping your furry friend active and happy in all weather conditions.

Rain or shine, snow or heat, our professional dog walkers are dedicated to providing your dog with the exercise they require. We come prepared with the right gear to ensure a safe and enjoyable walk in any weather.

But that’s not all – we take dog walking to a new level with our pack dog walking services.

We wholeheartedly embrace the power of pack mentality, and our professional dog walkers are here to bring joy and excitement to your pup’s outdoor experiences.

No matter your dog’s personality or needs, MD Pup Scouts welcomes them with open arms. Whether your pup is shy, anxious, socially awkward, or overflowing with excitement, we have the expertise to ensure every walk is enjoyable and safe.

Our mission is clear: we aim to create positive transformations in every dog we encounter. With MD Pup Scouts, you can rest assured that your beloved companion will be strutting their stuff, proudly showcasing new skills learned from our dedicated team.

Join our pack today, and let’s make every walk an adventure your furry friend will cherish. Your dog’s happiness and well-being are our top priorities, and we can’t wait to be a part of their journey.

Contact MD Pup Scouts now to give your pet the outdoor experiences they deserve!

MD Pup Scouts ensures safe dog walking in any weather
Experience the Joy of Year-Round Dog Walking Adventures!

Frequently Asked Questions 

1. Why is daily dog walking important? 

Daily dog walking is essential for your pet’s physical and mental health. It helps them maintain a healthy weight, prevents behavioral problems, and provides necessary mental stimulation and social interaction.

2. How long should a typical dog walk be?

The ideal duration of a dog walk depends on your dog’s breed, age, and energy level. On average, a 30-minute to 1-hour walk is suitable, but some dogs may require longer walks for sufficient exercise.

3. What items should I bring on a dog walk? 

Essential items for a dog walk include a leash, waste bags for cleaning up after your dog, water, a collapsible bowl for drinking, and identification, such as a collar with tags. You should also bring treats, a first-aid kit, or protective gear like booties in certain situations.

4. Is it safe to walk my dog during extreme weather conditions? 

While walking your dog in most weather is generally safe, extreme conditions like excessive heat, cold, or severe storms can pose risks. Use your judgment, and consider adjusting the duration or choosing indoor activities during extreme weather to ensure your dog’s safety and well-being.