Here's a sample itinerary for a pet-friendly drive from New York City to Rockland with your dog or cat. If you're planning a road trip to Rockland, you can research locations to stop along the way. Make sure you check road conditions to double check the weather. Find the best dog parks, pet-friendly accommodations and hotels, restaurants, and attractions based on the most talked about places recommended by Trippy members and GoPetFriendly. Scroll down to see all the pet-friendly stops along the way.
10:00 am start in New York City
drive for about 1.5 hours
11:36 am New Haven
eat at Claire's Corner Copia
stay for about 1 hour
and leave at 12:36 pm
drive for about 42 minutes
1:19 pm Hartford
stay for about 1 hour
and leave at 2:19 pm
drive for about 54 minutes
3:12 pm Old Sturbridge Village (Massachusetts)
stay for about 1 hour
and leave at 4:12 pm
drive for about 1 hour
5:25 pm Cambridge (Massachusetts)
eat at Cafe Paradiso
stay overnight at Charles Hotel in Harvard Square
leave the next day around 10:00 am
day 1 driving ≈ 4.5 hours
find more stops
10:00 am leave from Charles Hotel in Harvard Square
drive for about 1.5 hours
11:15 am Portsmouth (New Hampshire)
eat at Breaking New Grounds
stay for about 1 hour
and leave at 12:15 pm
drive for about 51 minutes
1:06 pm Portland (Maine)
stay for about 1 hour
and leave at 2:06 pm
drive for about 50 minutes
2:55 pm Boothbay Harbor
stay for about 1 hour
and leave at 3:55 pm
drive for about 47 minutes
4:42 pm arrive in Rockland
stay at Glenmoor by the Sea
day 2 driving ≈ 3.5 hours
find more stops
New Haven (8 answers)
Elkismom Pet Sitting (1 mention)
East Rock Park (1 mention)
pet-friendly restaurants around New Haven:
Claire's Corner Copia
questions about New Haven:
What is your favorite restaurant in New Haven?
Let's get serious about Pizza..... Sally's? Pepes? or Modern?
Hartford (14 answers)
Sit and Stay Pet Sitting Service (1 mention)
Home Comfort PetCare (1 mention)
pet-friendly restaurants around Hartford:
Hot Tomato's Restaurant
questions about Hartford:
What is your favorite restaurant in Hartford?
Old Sturbridge Village (Massachusetts) (4 mentions)
Sturbridge Pet Services (1 mention)
Hyland Orchard and Brewery (1 mention)
pet-friendly restaurants around Old Sturbridge Village (Massachusetts):
Rom's Restaurant
Cambridge (Massachusetts) (22 answers)
Cambridge Trust (1 mention)
Harvard University Campus (1 mention)
Schoenhof's Foreign Books (1 mention)
Nunziato Field Dog Park (1 mention)
pet-friendly restaurants around Cambridge (Massachusetts):
Cafe Paradiso
Au Bon Pain
Henrietta's Table - The Charles Hotel
Pizzeria Uno
pet-friendly hotels around Cambridge (Massachusetts):
Charles Hotel in Harvard Square
Sheraton Commander Hotel
questions about Cambridge (Massachusetts):
Where to eat lunch and dinner around MIT
What is your favorite restaurant in Cambridge (Massachusetts)?
What to do in Cambridge?
Portsmouth (New Hampshire) (19 answers)
Portsmouth Dog Park at South Mill Pond (1 mention)
Canine Cupboard Gourmet Dog Treats (1 mention)
Harbour Trail (1 mention)
It's Raining Cats and Dogs (1 mention)
Pierce Island Off Leash Area (1 mention)
pet-friendly restaurants around Portsmouth (New Hampshire):
Breaking New Grounds
Annabelle's Natural Ice Cream
Portland (Maine) (59 answers)
Books Etc. (1 mention)
Eastern Promenade Park Off Leash Dog Area (1 mention)
The CAT Ferry (1 mention)
pet-friendly restaurants around Portland (Maine):
Federal Spice
O'Naturals
Sebago Brewpub
The Garden Cafe at The Portland Regency
Gritty McDuffs
Beal's Old Fashioned Ice Cream
questions about Portland (Maine):
Good restaurants in Portland
Best places to eat in Portland, ME
Things to do and good restaurants in Portland, ME
Best Breakfast spots in Portland, Maine?
Boothbay Harbor (6 mentions)
Tidal Transit (1 mention)
Linekin Preserve (1 mention)
Two Salty Dogs (1 mention)
Balmy Days Cruises (1 mention)
Lobster Cove Meadow (1 mention)
pet-friendly restaurants around Boothbay Harbor:
Chowder House & Boat Bar Grill
The Lobster Dock
Boothbay Region Lobstermen's Co-Op Restaurant
Are you going straight to a hotel, or looking for a vacation rental or Airbnb?
The best resource on neighborhoods, areas, and hotels is the Trippy page on where to stay in Rockland.
If you're looking for a quick answer, you can check out Glenmoor by the Sea.
Want to research more popular hotels in Rockland? Click the blue button below.
Need some recommendations on somewhere to get food?
GoPetFriendly suggests Second Read Books and Coffee.
Here are some more restaurants people talk about:
Want to research more popular restaurants in Rockland? Click the blue button below.
This section could be endless, so rather than trying to suggest every local activity or attraction, we'll leave it open-ended.
These are some of the places people talk about on GoPetFriendly:
Of course, Trippy is the perfect place to ask questions because there's an entire community of travelers talking to each other and sharing tips and advice. Trippy is where you can get answers personalized for your tastes, budgets, trip dates & more!
Click the button below to explore more questions and answers related to Rockland.
Yes, even this step is optional, because if you're on vacation who wants the trip to end? It's okay, you can start planning your next trip!
Want to plan the trip back? Get the reverse directions for a Rockland to New York City drive with pets, or go to the main page to plan a new road trip.
You can also compare the travel time if you're flying or driving by calculating the distance from New York City to Rockland. Or get a full New York City to Rockland flight plan.
Don't forget about exploring your own hometown with a staycation. You can also find some cool day trips or get away for a weekend. Maybe try typing in a faraway location like London, Hong Kong, or Sydney, and get inspired for your dream trip around the world.
And if you know New York City well, please help your fellow travelers and answer their questions about New York City!
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