Quickies

• The Town of Milford Connecticut

A cute downtown harbor area with a number of bars and restaurants and beautiful colonial architecture. The train station is right downtown and mercifully the post road is farther north" taarok

• Cold Spring

• The Poconos

"Indoor Water parks!" tmm224

"Mount Airy Lodge, where all you have to bring is your love of everything." timspc

"There's also a casino and a shooting range in the area. My friends took me away for a birthday weekend. Very affordable. Very fun." ravelight

• Ithaca

If you're willing to go a little further than 3 hours (more like 4 or so) It's a nice college town with lots of good restaurants and shops and has a lot of cool hiking trails with waterfalls nearby. It's also located at the bottom of one of the finger lakes with a bunch of wineries to go wine tasting at along the lake. u/drjimmybrungus

• Saratoga Springs

"it's a spa town. If you're an American history buff, the Battle of Saratoga took place about 15 minutes outside of the present-day town." chengjih

Adirondack Trailways Bus , plenty of B&Bs to choose from, quaint city with a bunch of options for side-trips. carpy22

• The Berkshires!

Lenox and Great Barrington are nice, great dinner spots, hiking outdoor activities, plus museums like the Mass MOCA and the Norman Rockwell museum for indoor adventures. Chesterwood is a fantastic outdoor sculpture park with light hiking and outdoor installations, and Tanglewood for amazing music (mostly classical) if they haven't yet closed for the season. lizzyism

• Delaware Water Gap, NJ

"1.5-2 hours by car. Worthington State Forest is a good campsite with shower. Hike Red Dot Trail for a good view, or Tammany Trail. Kayaking in the river is fun, too." consuellabanana

• Peekskill

There is an old motel there which you can walk up the hill to. The rooms were built in the 50s and are kinda small but most have views of the Hudson Valley. Also, it's a discount place so ask for a remodeled room (room 39 is very nice) and there are bunches of great restaurants in the area. I think you can get discounts from Hotels.com for the room. You can spend a day walking around the city of Peekskill. Great bookstore, old shops, art district etc. If you want, you can hop a train for a side trip to a number of smaller towns and cities like Sleepy Hollow. Anonymoustard

• Long Branch

1:30-1:50 from city- Take the NJ Transit train down to Long Branch. From the station its a short walk east to the beach and Pier Village. Make sure to take a stroll to hit up the Windmill, Max's, Surf Taco or The Inkwell for lunch, Lighthouse for ices. Good bars w/ local crowd on Brighton Ave. Beginning Memorial Day weekend, you can also change trains in Long Branch and head down to Asbury Park. Walk down Cookman Ave. to the Boardwalk & beach area. You can do this out-of-season as well but it's quiet and trains run less frequently. sokpuppet1

• Bear Mountain state park

"For hiking / picnicking. Also possible to get a bus from NY17 on the other side of Harriman at Arden Valley Rd. Hike from Bear Mountain Inn to that point on the Appalachian Trail is ~25 miles." frankiepoops

• The Highlands

Ferry from Wall Street Pier 11 to the Highlands and taking a quick Uber to Donovan's in Sea Bright (in the summer). Beach bar and easy to get to/from. Can be a day trip! Flaythemall

• Harriman State Park

Drive down Seven Lake parkway and choose whichever lake suits you best. Some have sectioned off swimming areas, and the first lake tends to be the most crowded, but further down the parkway is usually quiet. If you can manage to get up during the week, it is virtually empty. There are a few lakes that have some tucked away little coves that are good for swimming, though it is not allowed and park rangers will yell at you if they see you (or so I have heard...personally, never ran into one). Its about 1.5 hrs outside nyc. roboecho

• Storm King

Storm King, the largest outdoor sculpture park, is great. It's an easy drive, about an hour and half. Then you could possibly continue on to Peekskill (~30min from Storm King) and have drinks/snacks at the Peekskill brewery. And I love Hudson Valley, great restaurants/scenery and lots of nice charming towns to visit like Milton, the aforementioned Peekskill, Cold Spring, or Kingston are all worth checking out. Read this NY Times article. And if you're going up this weekend, you might be able to get tickets to the "Jack O'Lantern Blaze" at Van Cortlandt Manor in Cronton-On-Hudson. Check out these pics. You could visit the Culinary Institute in Hyde Park and get a meal at one of the campus restaurants staffed by the students. Bear Mountain is another nice outdoorsy getaway OIlberger

• Vanderbilt on Long Island

Really nice grounds for the kids to run around, you can all tour the old house(where if I remember right they have a mummy) and there's a planetarium. Also on Long Island you can go to Sagamore Hill which is Teddy Roosevelt's house. Its pretty cool to tour since he was an avid hunter. FirstLadyofBeer

• Delaware Water Gap

" The Martz Bus is frequent and convenient. carpy22

• Troy, New York

• Nyack, New York

I love Nyack! I live here now actually. You can get there by taking the Metro North to Tarrytown and then take the Hudson Link across the River.
Lots of little shops and restaurants. On the weekends there’s lots of bikers around. Monthly there’s a pretty big street fair that garners a lot of visitors.
Strawberry place is the best for breakfast (cash only). UP Lounge or OD’s for dinner. The Local or Karma for drinks.
Piermont is very close (biking or cheap bee distance). They have cute stores and restaurants. You can rent kayaks and kayak in the Piermont Marsh, or walk out on Ferry Road which is the furthest you can get to the middle of the Hudson without being on a boat or ferry. nakedrottweiler

Longies

• Virginia Beach
• Burlington, Vermont
• Providence, RI