Best dog walkers in Dedham Square (Historic Dedham Square)

One of the most dog friendly neighborhoods in Dedham. Instantly book and meet an exceptional dog walker in Dedham Square (Historic Dedham Square) today.

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Top dog walkers in Dedham Square (Historic Dedham Square)

1. Gavin G

Brighton, MA, 02135

Five stars

5 (28)

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Brighton, MA, 02135

2. Kayla D

Brookline, MA, 02446

Five stars

5 (69)

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Brookline, MA, 02446

3. Sara D

Newton, MA, 02466

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5 (12)

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Newton, MA, 02466

1. Gabrielle D

Dedham, MA, 02026

Five stars

5 (292)

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Dedham, MA, 02026

2. Azeb Z

Hyde Park, MA, 02136

Five stars

4.9 (170)

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Hyde Park, MA, 02136

3. Kayla A

Hyde Park, MA, 02136

Five stars

5 (75)

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Hyde Park, MA, 02136

4. Katelyn B

Hyde Park, MA, 02136

Five stars

5 (36)

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Hyde Park, MA, 02136

5. Jill M

Needham, MA, 02492

Five stars

5 (109)

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Needham, MA, 02492

6. Ariana P

Boston, MA, 02136

Five stars

5 (9)

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Boston, MA, 02136

7. Robyn B

Needham, MA, 02494

Five stars

5 (34)

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Needham, MA, 02494

8. Stewart G

Brookline, MA, 02445

Five stars

5 (324)

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Brookline, MA, 02445

9. Charlotte C

Jamaica Plain, MA, 02130

Five stars

5 (88)

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Jamaica Plain, MA, 02130

10. Amelia L

Newton Upper Falls, MA, 02464

Five stars

5 (417)

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Newton Upper Falls, MA, 02464

11. Daniel L

Newton, MA, 02461

Five stars

5 (310)

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Newton, MA, 02461

12. Jeffrey A

Dorchester, MA, 02124

Five stars

4.9 (426)

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Dorchester, MA, 02124

13. Colton R

Jamaica Plain, MA, 02130

Five stars

5 (33)

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Jamaica Plain, MA, 02130

14. Eric W

Dorchester, MA, 02124

Five stars

5 (11)

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Dorchester, MA, 02124

15. Samantha L

Canton, MA, 02021

Five stars

5 (343)

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Canton, MA, 02021

16. Collin M

Dorchester, MA, 02124

Five stars

5 (1841)

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Dorchester, MA, 02124

17. Elizabeth M

Norwood, MA, 02062

Five stars

5 (152)

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Norwood, MA, 02062

18. Jovahn D

Dorchester, MA, 02121

Five stars

5 (157)

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Dorchester, MA, 02121

19. Nia H

Dorchester, MA, 02124

Five stars

5 (32)

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Dorchester, MA, 02124

20. Ellie P

Waban, MA, 02468

Five stars

5 (42)

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Waban, MA, 02468

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Wag! Walkers know Dedham Square (Historic Dedham Square)
Dedham Square is the historic and retail center of Dedham, Massachusetts. Situated southwest of Boston, Dedham is a charming town favorited by commuters and families looking for a quieter living situation outside of the bustling state capital. Dedham Square is the town's busiest area, boasting different retail and dining options as well as some of the town's most historic architecture. The Dedham Community Theatre and the Historical Society are two hotspots for local history buffs. A variety of events are also hosted in the square year round such as the Dedham Farmers Market and free movie nights. 

Dedham Square allows you and your pet to enjoy a relaxing walk away from the rush of the city while still able to explore unique storefronts and cafes. While New England is a beautiful place to be outside, check the weather before going out for a walk as the weather in eastern Massachusetts can change instantly. 
What is the terrain like in Dedham Square (Historic Dedham Square)?
Dedham Square is a very small area, so don't expect a very long walk through this neighborhood. It's a mostly flat area consisting of old buildings with many storefronts which is ideal for the dog who loves window shopping and meeting people on the street. This is a place that encourages you to "stop and smell the roses" and explore what a small New England town has to offer. The square is very clean with manicured lawns and spotless sidewalks and there are benches along the streets if you ever want to stop and rest for a minute or for some ample people-watching. 

While most of Dedham Square consists of wide sidewalks along semi-busy roadways, there are some spots to try and avoid walking your pet. Providence Highway cuts through the eastern middle part of the neighborhood and is full of fast cars and no border between the road and the small sidewalk. 
How many greenways are there in Dedham Square (Historic Dedham Square)?
Dedham Square is suited more for people and pets who like window shopping more than hiking. However, there are a few spots around the town itself that offer ample green space for a romp around the park. The top half of Barnes Memorial Park sits near Dedham Square, just on the other side of Providence Highway. This park features several athletic fields and a playground and is nice for a quick rest on a patch of grass away from the bustling square. Just south of that is Wigwam Pond Area, a sprawling wooded area with a large pond. 

Dedham is well-known as a town featuring several state parks perfect for hiking. If you're interested in some hiking, you can head south of Dedham Square to Dedham Town Forest, an expansive 77-acre hiking area. Below that are several conservation areas as well as the Lowell Woods, another favorite spot for hiking through shady forest.
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© 2025 Wag Labs, Inc. All rights reserved.