My partner and I will be traveling frequently with our small dog. We enjoy hiking, beaches, dog parks, kayaking, dining out, and being outdoors.

A little bit of NYC in the Berkshires! The best bagels outside of the City and probably the only place to get a Chocolate Egg Cream for miles! The outside seating is nice, with umbrellas for shade. We ordered a side of bacon for our dog, and brought our own water bowl.

We had the perfect puppy dog day in Bennington. A delicious lunch at Kelli’s, where they brought out a water bowl with the menus, and had a full doggie menu. The brisket melt was amazing, and their potato salad is top-tier. We stopped here before heading up to Mile-Around Woods, and it really made for a perfect day! We’ll definitely make another day trip up to Vermont to visit Kelli’s!

We spent a few lovely hours enjoying the views and wildlife here, after our excellent meal at Kelli’s Tavern. We plan on visiting both again the next time we’re in Bennington.

We planned a stop at The Blueberry Muffin while we we in town with our dog. Sadly, when we got there, they did not have outdoor dining. I am not sure if it was just too early in the season (Memorial Day Weekend) or if that’s a permanent change. Worth calling ahead to confirm dog friendly seating before you make the trek out.

Great location, right in downtown. The Food and smoothies were scrumptious. Beautiful patio with umbrellas for shade. We bring our travel water bowl with us. No doggy menu or bowls, but they were very friendly and welcoming.

We found this place on Bring Fido, and brought our dog here after a long car trip and a quick visit to downtown Plymouth. It was a perfect experience all around. The “pawtio” was quiet, and cool - ideal after a long day of travel and sightseeing. The human food was great, lots of vegetarian options (I got the Mediterranean platter) and meaty options (he got the smokehouse burger.) We loved that there was a whole menu for dogs, including grilled chicken, eggs, or peanut butter and banana. The staff were absolutely delightful.