A Day in Ossining | InOssining.com

A Day in Ossining

Do you have family or friends coming over and you want to show them your town? Or maybe you’re thinking about moving to Ossining?

Here’s a suggested itinerary to enjoy a day in¬†our beautiful Rivertown. These activities span from morning to night, so get started early and plan on making a full day of it. Just about the only other thing you’ll have time for is collapsing into bed at the end of a satisfying, delicious, fun-filled day ūüôā


Start the day at The Delibagel¬†Caf√©¬†(on Facebook), located in the Arcadian Shopping Center. Chef Joe Sanzo opened the cafe in 2014 and it’s been a popular spot ever since. It’s open at 6am during the week and 7am on weekends, so it’s not a problem if you want to get an early start on the day. It’s traditional breakfast dishes, and of course bagels, but cooked with talent and care.

Morning hike

After a delicious breakfast, take the 15-minute drive to Teatown Lake Reservation (on TripAdvisor), located at 1600 Spring Valley Rd #1. Here you can find more than 15 miles of trails, but for today we recommend you  follow the oldest and most popular trail on the preserve: the Lakeside Trail.

Follow the blue markers and your hike will take you past the famous Teatown Boathouse, over boardwalks and through natural rock formations. For the youngsters, they provide ‚Äėeducation stops‚Äô to help visitors better familiarize themselves with the ecosystems and wildlife found on the preserve. Distance: 1.5 miles, Time: 45 min to an hour.

When you’re done with your hike,¬†stop by Teatown’s¬†Visitor’s Center to shop at the nature store, visit their exhibits and animal ambassadors (some indoor and some outside in the “Raptor Loop”) and take a nice break. ¬†The Visitor’s Center is open every day from 9am until 5pm.

Can you believe its already midday. Are you hungry again yet?

Checking out Main Street

The next stop is Main Street (12 min. drive from Teatown), where you can have lunch, shop and grab a coffee. You can park on the street or in the parking lot next to the post office.
Ossining National Bank

We recommend you check out 125 Main Street, where you can find¬†Melita’s Home Furnishings, a a long-time Ossining staple that¬†specializes in luxury decor for the home, including ceramics, linens, bedding and more. If you have kids, or need to find a present for one,¬†Penny & Ting¬†(on Facebook) is at 133 Main Street, almost right next door from Melita’s. Penny & Ting is a beautiful toy store thoughtfully filled with interesting and fun toys and games.¬†

Lunch and coffee

For Lunch, you have many different options: the newly opened Good Choice Kitchen¬†(on Facebook) on 147 Main St. offers healthy, delicious, organic, plant-based food that is not only good for you but also tastes great. If you want a quick bite, you can’t miss Cravin’ Jamaican Cuisine¬†(on Yelp)¬†on¬†109 Main Street.¬†Their oxtail is to die for.

For traditional Portuguese food we recommend¬†Doca’s¬†(on Facebook)¬†at 125 Main St., a welcoming family-run¬†restaurant in a single room featuring rustic Portuguese food & a BYO-spirits policy.

Another restaurant that we love is the Peruvian¬†Aji Limo¬†(on Facebook) up the street¬†at¬†199 Main St. For some inane reason we can’t comprehend, there isn’t a great Peruvian restaurant in every town in the U.S. Fortunately, the drought is over in Ossining. If you haven’t tried Peruvian before, just go. If you have, well then you’re probably headed there already.

Eat all you want, but make sure you save some space for coffee and dessert, because a day in Ossining is not complete without a stop at¬†First Village Coffee¬†(on Facebook). Our new lovely coffee shop offers amazing pastries and delicious Irving Farm coffee. Grab a book and relax at a table, or sit down on a stool and chat with the owner Luis, he’s a great guy and knows everything going on in town.

After all that delicious food you’ll be ready for some more exploring!

Afternoon walk

Head over to the¬†Sing Sing Kill Greenway (its a 5 minute walk from First Village Coffee and starts next to the Rec Center parking lot), a concrete walkway that will take you¬†through the scenic Sing Sing Kill gorge. Its a beautiful walk and has¬†steel railings along its full length so it’s¬†ADA-compliant and safe to visit with little kids.

Hudson River Waterfront

Because the Hudson River is such an important part of this town, our last stop is The Waterfront.  Here you can find a walking path, 2 playgrounds, a little beach, seating/viewing platforms, restrooms and an event stage that hosts concerts most Friday nights during the summer.

If it’s a weekday afternoon and you’re feeling adventurous, hop on the¬†Haverstraw‚ÄďOssining Ferry. It’s a passenger ferry that runs between¬†Ossining and ¬†Haverstraw via the Haverstraw Bay and Hudson River.¬†The trip across the river takes approximately 15 minutes (but also take into account boarding). Thee fare is $4.25 per¬†adult, $2.00 per child (6-11) and senior (62+) and free for children 5 and under. Go here for the schedule and more info.

Finish off the day at the¬†3 Westerly Bar & Grill,¬†a nautical-themed gastropub housed within a distinctive free-standing “lighthouse” that features indoor/outdoor dining options with stunning views of the scenic Hudson River waterfront. ¬†Here you can try a variety of see food like scallops, sushi and Chilean sea bass, as well as wood-fired artisanal pizzas, German-style pretzels and¬†burgers.

So sit, eat and relax with a beautiful view of the Hudson River. If you are lucky, you might get a sunset like this one…
Ossining Sunset

Now that’s a great day!

Now admittedly if you actually do all of these things in one day, your calorie consumption might break the 5000 mark (that’s 5000+ delicious calories). In our defense, we also sprinkled in a good deal of exercise throughout the day, so that should help a bit.

If you don’t have a whole day, try out of all of these fun activities and great local businesses whenever you can fit them in to your busy schedule!

And of course we couldn’t touch on all of the great restaurants and activities in Ossining. It was after all just one day. Now to you. Comment below and let us know: what you would do if you had one day to spend exploring Ossining?

  • Cami says:

    This is great! I love Ossining

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