Best dog walkers in Highland Park

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Top dog walkers in Highland Park

Promoted Caregiver
Michaela M avatar

1. Michaela M

Wag! Expert icon
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Boston, MA, 02127

Five stars

5 (168)

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Boston, MA, 02127

Promoted Caregiver
Teara B avatar

2. Teara B

Wag! Expert icon
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Dorchester, MA, 02132

Five stars

4.9 (958)

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Dorchester, MA, 02132

Promoted Caregiver
Darrow B avatar

3. Darrow B

Wag! Expert icon
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Boston, MA, 02114

Five stars

5 (25)

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Boston, MA, 02114

Promoted Caregiver
Jingxin Z avatar

4. Jingxin Z

Wag! Expert icon
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Allston, MA, 02134

Five stars

5 (54)

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Allston, MA, 02134

Promoted Caregiver
Alanys A avatar

5. Alanys A

Wag! Expert icon
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Cambridge, MA, 02139

Five stars

4.8 (58)

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Cambridge, MA, 02139

Promoted Caregiver
Nainika S avatar

6. Nainika S

Wag! Expert icon
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Allston, MA, 02134

Five stars

4.4 (6)

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Allston, MA, 02134

Promoted Caregiver
Chloe T avatar

7. Chloe T

Wag! Expert icon
Location icon

Cambridge, MA, 02139

Five stars

5 (5)

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Cambridge, MA, 02139

Promoted Caregiver
Luis  D avatar

8. Luis D

Wag! Expert icon
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Brighton, MA, 02135

Five stars

5 (151)

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Brighton, MA, 02135

Promoted Caregiver
Adrienne M avatar

9. Adrienne M

Wag! Expert icon
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Newton, MA, 02458

Five stars

5 (52)

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Newton, MA, 02458

Promoted Caregiver
Jared R avatar

10. Jared R

Wag! Expert icon
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Quincy, MA, 02170

Five stars

5 (90)

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Digital Training

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Quincy, MA, 02170

Promoted Caregiver
Skylar W avatar

11. Skylar W

Wag! Expert icon
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East Boston, MA, 02128

Five stars

5 (506)

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East Boston, MA, 02128

Promoted Caregiver
Caroline W avatar

12. Caroline W

Wag! Expert icon
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Medford, MA, 02155

Five stars

5 (98)

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Medford, MA, 02155

Promoted Caregiver
Casey M avatar

13. Casey M

Wag! Expert icon
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Medford, MA, 02155

Five stars

5 (64)

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Medford, MA, 02155

Promoted Caregiver
Tanya M avatar

14. Tanya M

Wag! Expert icon
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Needham, MA, 02494

Five stars

5 (5)

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Needham, MA, 02494

Promoted Caregiver
Gabrielle  D avatar

15. Gabrielle D

Wag! Expert icon
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Dedham, MA, 02026

Five stars

5 (243)

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Dedham, MA, 02026

Promoted Caregiver
Joseph B avatar

16. Joseph B

Wag! Expert icon
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Braintree, MA, 02184

Five stars

5 (819)

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Braintree, MA, 02184

Promoted Caregiver
Karolina D avatar

17. Karolina D

Wag! Expert icon
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Saugus, MA, 01906

Five stars

5 (174)

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Saugus, MA, 01906

Promoted Caregiver
Harlan B avatar

18. Harlan B

Wag! Expert icon
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Wellesley, MA, 02481

Five stars

4.8 (26)

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Wellesley, MA, 02481

Boaz S avatar

1. Boaz S

Wag! Expert icon
Location icon

Brookline, MA, 02446

Five stars

5 (96)

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Brookline, MA, 02446

Olivia D avatar

2. Olivia D

Wag! Expert icon
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Boston, MA, 02215

Five stars

5 (324)

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Boston, MA, 02215

Andrew C avatar

3. Andrew C

Wag! Expert icon
Location icon

Boston, MA, 02115

Five stars

5 (148)

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Boston, MA, 02115

Julia M avatar

4. Julia M

Wag! Expert icon
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Brookline, MA, 02446

Five stars

5 (649)

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Brookline, MA, 02446

Emily G avatar

5. Emily G

Wag! Expert icon
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Roxbury, MA, 02119

Five stars

5 (221)

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Roxbury, MA, 02119

Ross V avatar

6. Ross V

Wag! Expert icon
Location icon

Roxbury, MA, 02120

Five stars

5 (9)

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Roxbury, MA, 02120

Christina M avatar

7. Christina M

Wag! Expert icon
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South Boston, MA, 02127

Five stars

5 (106)

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South Boston, MA, 02127

Ava A avatar

8. Ava A

Wag! Expert icon
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Roxbury Crossing, MA, 02120

Five stars

5 (29)

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Roxbury Crossing, MA, 02120

Erin C avatar

9. Erin C

Wag! Expert icon
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Portland, ME, 04102

Five stars

5 (43)

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Portland, ME, 04102

Katherine M avatar

10. Katherine M

Wag! Expert icon
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South Boston, MA, 02127

Five stars

5 (21)

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South Boston, MA, 02127

Anna B avatar

11. Anna B

Wag! Expert icon
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Boston, MA, 02115

Five stars

5 (94)

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Boston, MA, 02115

Allison S avatar

12. Allison S

Wag! Expert icon
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Jamaica Plain, MA, 02130

Five stars

5 (32)

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Jamaica Plain, MA, 02130

Kayla H avatar

13. Kayla H

Wag! Expert icon
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Roxbury Crossing, MA, 02120

Five stars

5 (21)

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Roxbury Crossing, MA, 02120

Kayla M avatar

14. Kayla M

Wag! Expert icon
Location icon

Boston, MA, 02120

Five stars

5 (78)

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Boston, MA, 02120

Amelia F avatar

15. Amelia F

Wag! Expert icon
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Roxbury, MA, 02120

Five stars

5 (6)

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Roxbury, MA, 02120

Devon K avatar

16. Devon K

Wag! Expert icon
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Jamaica Plain, MA, 02130

Five stars

5 (2)

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Jamaica Plain, MA, 02130

Madeline B avatar

17. Madeline B

Wag! Expert icon
Location icon

Boston, MA, 02120

Five stars

5 (41)

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Boston, MA, 02120

Koki T avatar

18. Koki T

Wag! Expert icon
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Roxbury, MA, 02119

Five stars

5 (122)

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Roxbury, MA, 02119

Caroline P avatar

19. Caroline P

Wag! Expert icon
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Boston, MA, 02114

Five stars

5 (37)

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Boston, MA, 02114

Nicole G avatar

20. Nicole G

Wag! Expert icon
Location icon

Boston, MA, 02118

Five stars

5 (162)

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Boston, MA, 02118

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Wag! Walkers know Highland Park

Highland Park is a community located south of Boston’s central business district, about a 15-minute commute from the downtown area. The community is home to Roxbury College and there are several local shops, eateries, and services in the area that can be reached on foot. 


When strolling the neighborhood with your dog, Boston's climate can throw a lot of variable weather at you, so be prepared with the right outerwear. Although summers are mostly warm with some cool breezes off the ocean, occasional humid weather occurs which may require you to choose to walk at different times of the day. Rainy days are frequent in this coastal location and rain gear will be a must to stay dry. Winters are cold and snowy and you will want to bundle up to stay warm. Thunderstorms are also frequent occurrences in warmer months and can pose a hazard to pets. Take shelter when storms are imminent.

What is the terrain like in Highland Park?

Highland Park is bordered by Columbus Avenue on the west, Malcolm X Boulevard on the north, Washington Street on the east, and Richie Street on the south. The region is mostly residential with a few commercial businesses located within its boundaries. 


 Residences in the area consist of multi-story townhouses, duplexes, and low rise apartment buildings as well as detached homes. Many houses in the area exhibit historic architecture and have unique and interesting features. Streets are narrow and heavily treed with closely set buildings and properties. This makes for shady streetscapes. Sidewalks are prevalent in the area so you and your dog don't have to share the road with traffic. 


Highland Park is situated on elevated ground above the surrounding neighborhoods and there are some hills in the community, although inclines are not usually steep. A college, local school grounds, and many small parks in the area provide local green spaces.

How many greenways are there in Highland Park?

Several community parks and recreation areas create attractive greenways within easy walking distance of Highland Park residents. The Southwest Corridor Park provides over 50 acres and stretches for 4.7 miles. This greenway has an excellent hiking trail for you and your hound to take a long trek. Highland Park has open lawns surrounded by trees and an observation tower. Walking paths are also present for strolls with your pet. 

Roxbury Heritage State Park has interesting historic buildings and the Jeep Jones Park is heavily treed with sports facilities and a great paved walking path. The Marcella Playground has a ball diamond and sports facilities with a paved walking path along the border and some large shade trees. 

Several other smaller community greenways and parks mean that you are never far from a greenway when strolling the area with your pet. Remember to keep your dog leashed and be prepared to clean up after your pet.

Frequently Asked Questions

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