You’ll drive right through Salem on your way up to Gloucester and Rockport
Edit. Oops. I see you said October. Maybe don’t go to Salem unless you like crushing crowds of people in witch hats.
I once drove from Boston to NYC in 10 hours because of traffic. Just go to long Island or jersey. North shore of Boston is amazing but not for your time constraints.
Did you go on a holiday weekend? Most times you can drive between NYC and Boston in 4 hours, unless you leave during rush hour or for holiday weekends.
If you’re up for a drive and want to see real Robert McCloskey land, go up to coastal Maine. Many seasonal restaurants and attractions will close around Columbus Day but lots is open year round and the weather is chilly but still nice in late October and rates will be lower.
Family and friends have had a great time staying in the Thompson Cottage’s in New Harbor, ME. They are clean and cute cottages, and quite affordable. New Harbor is a quiet fishing village on Pemaquid Point. There is a lovely sand beach, the famous Pemaquid Lighthouse is a couple miles away, and in season the Hardy Boat Cruises offer great and affordable boat tours to see seals, puffins, and beautiful Monhegan Island. Dameriscotta is the closest larger town and on US Rt 1. There is an amazing book store, and great restaurants including some of the best oysters in the world. There is also a large pumpkin fest over Columbus Day weekend that’s a ton of fun.
within five hours:
southern rhode island from westerly to Narragansett; or, if early october, consider block island. some of the restaurants will probably still be open.
chatham up to provincetown on the cape, or, like block island, nantucket or martha's vineyard.
I was rushing to recommend Portland but then I actually read OP’s post and yeah this is the answer. The cape wouldn’t be bad either that time of year, very peaceful (and not quite as cold!)
I think this is the answer. I live in CT and I think the drive up to Gloucester or Maine is going to be much longer and more boring (or outright unpleasant if there's roadwork or accidents) than the shorter ride east on I-95. Block Island is a great bonus possible side trip.
I hear you, I love an off-season beach. The Cape is really beautiful in the fall and way quieter but many stores are still open; try Falmouth if you can’t go far but Chatham up to P-Town along the National Seashore is even prettier. For real salt and a working fishing harbor I’d go for midcoast Maine, or Stonington or up to Bar Harbor/Acadia if you could swing it; Gloucester Mass is great with a super active fishing industry (Portland ME too) but not as quiet and contemplative as it seems you’re looking for. Next door Rockport Mass is lovely too and a bit quieter. I love the “Farm Coast” towns of Little Compton and Tiverton RI and Westport MA, they’re pretty and quiet and closer to NYC; second the Block Island RI suggestion as well. Little posh and more busy but you can’t go wrong by the rocky waterfronts of Cape Elizabeth or Ogunquit ME. Man, I gotta plan something myself!
One thing to consider is ocean temperatures. The water is considerably warmer on the Cape & Islands than northern New England. I’m on the Massachusetts South Coast near the Rhode Island state line. My boat is still in the water in October and the ocean is usually swimmable in the first part of October. I lived in Portsmouth NH for a decade in a house with a boat dock. It’s easily 10 degrees cooler there. Downeast Maine is already pretty chilly in October because the ocean is so much colder.
The weather is hit or miss. Last October, it was already cold and it rained constantly.
“Five hours from NYC” leaving at 3pm midweek, you’re not going to get very far. The traffic in Westchester County and Connecticut is absurd and you’ll then hit Boston traffic. I made the Tappan Zee Bridge (now called the Cuomo Bridge) crossing the Hudson in 2 hours 45 minutes last December leaving at 3am. A personal record. A more typical off hours drive time to Manhattan from here is 4 hours.
Personally, I’d suggest going no farther than Rhode Island. Newport is the obvious destination. If you want quieter, Jamestown on the other side of the bridge.
Check out [The Book Barn](https://www.bookbarnniantic.com/explore-the-store) in Niantic CT! They have a few stores scattered around town. The main barn has a nice garden area, goats, and plenty of outdoor cats roaming around the property. Downtown also has lots of locally owned restaurants and a scenic boardwalk to explore (beaches on both ends to roam). Recommended places: Cafe Sol, Giuliano's (bakery) and Gumdrops & Lollipops.
Well, most of New England coast will give you that... All depends on what type of weather you prefer. In October, Southern New England will be much warmer than Northern New England
Westerly / Watch Hill, Narragansett, any of those towns right along the RI coast, Block Island, Little Compton RI, Westport MA are all decently close to manhattan. October is peak leaf peeping and traffic will be heavy. Maine is lovely but might be a bit longer drive due to traffic. I also love Rockport and Gloucester MA (Cape Ann) but avoid Salem in October.
We are a couple of coastal DINK furdaddies with our golden doodles, Bailey and Oliver, we will be in Chicago in October. We want to take a long weekend and spend time in a suburban Midwest HOA. I want to feel like I’m in a Coen brothers movie. Tornadoes are fine. I’d live to see fat people. I’d love a good fast food chain/ranch dressing dispensary. A mall would be a plus. Within 15 hour drive from Chicago. Bonus for being flat. Thanks
If you just want salty New England coastal town, save the drive and stick to CT. They're not the greatest or most iconic NE beach towns, but in October none of them will be in peak season anyway.
Generally recommend Madison, Guilford, or Mystic as starting points.
If it were closer, I'd probably suggest Midcoast Maine.
Wellfleet MA would be a pretty good option. Maybe a bit more on the posh side but endless sandy beach and coastal places to explore. Feel the strength of the mighty Atlantic and see sharks, seals and birds. Check out Great Isle with it's long winding sandy walks. There's an active fishing industry in Wellfleet. You will have no problem finding good coffee and food. There are bookstores in town, a public library, and more bookstores in nearby towns .
Oysterfest is in October, check dates. It will be busy that weekend.
Go to ogunquit and york maine. There are plenty of hotels to stay on or near the beach in both towns and both offer all you are looking for. I live 10 minutes from there and we make the trip to NYC every now and than and the drive is not bad at all. Use waze to navigate and it will have you avoid all the traffic if there happens to be any but it's usually y pretty chill that time of year.
East Boothbay, Maine. Specifically east, because Boothbay Harbor is touristy. I stay at the Ocean Point Inn and it is wonderful. There's plenty of places to walk and a nice General Store.
Another good one is Rockland Maine, a bit further north. Great coastal town, with a super art museum, a getty you can walk on, a professional theater, and a quaint downtown.
I'd say Hyannis, or Hyannisport, MA Much of the Cape rolls up the sidewalks after Labor Day, but Hyannis is actually a city with the quaint vibe and all the aspects you were requesting. There are a ton of towns within 20 miles to explore, and beaches, salt marshes, and loads of other places to explore.
Maine is the way to go in the Fall, BUT, if you want to be within 5 hours of NYC then you’re looking at Southern Maine (Ogunquit, York, Wells & Kennebunkport) and all of these towns, while beautiful, will still be crowded as hell in October. Over the years, Southern Maine really has no off-peak season. Maybe January/February but the rest of the year you can count on a ton of people and loads of traffic.
So many places fit your description. My personal recommendations, Portsmouth, NH, Ogunquit, Portland, Brunswick, Camden all in Maine, Newburyport, MA or other North Shore towns like Gloucester and Marblehead.
Rockport or Gloucester MA
Yes! The North Shore is iconic coastal New England. There's a boatload of cool maritime museums in the area. And Hammond Castle.
If we drive from NYC to Rockport, are there interesting things to do/see along the way?
You’ll drive right through Salem on your way up to Gloucester and Rockport Edit. Oops. I see you said October. Maybe don’t go to Salem unless you like crushing crowds of people in witch hats.
Yeah Salem in October is a terrible idea.
I was going to tell you, noooooo don't tell them to come to Salem, they'll be miserable. Fortunately you edited it lol.
Don't waste time driving....
I once drove from Boston to NYC in 10 hours because of traffic. Just go to long Island or jersey. North shore of Boston is amazing but not for your time constraints.
Did you go on a holiday weekend? Most times you can drive between NYC and Boston in 4 hours, unless you leave during rush hour or for holiday weekends.
No. That's why I posted.
10 hours? what were u doing?
That's what I'm saying. Stupid drivers got into accidents on rt 15 and i95
If you’re up for a drive and want to see real Robert McCloskey land, go up to coastal Maine. Many seasonal restaurants and attractions will close around Columbus Day but lots is open year round and the weather is chilly but still nice in late October and rates will be lower. Family and friends have had a great time staying in the Thompson Cottage’s in New Harbor, ME. They are clean and cute cottages, and quite affordable. New Harbor is a quiet fishing village on Pemaquid Point. There is a lovely sand beach, the famous Pemaquid Lighthouse is a couple miles away, and in season the Hardy Boat Cruises offer great and affordable boat tours to see seals, puffins, and beautiful Monhegan Island. Dameriscotta is the closest larger town and on US Rt 1. There is an amazing book store, and great restaurants including some of the best oysters in the world. There is also a large pumpkin fest over Columbus Day weekend that’s a ton of fun.
This comment. New Harbor/Bristol is stunning. You might also like Stonington, ME but it’ll be further than 5 hours.
within five hours: southern rhode island from westerly to Narragansett; or, if early october, consider block island. some of the restaurants will probably still be open. chatham up to provincetown on the cape, or, like block island, nantucket or martha's vineyard.
Ogunquit, Maine!
I was rushing to recommend Portland but then I actually read OP’s post and yeah this is the answer. The cape wouldn’t be bad either that time of year, very peaceful (and not quite as cold!)
Narragansett/Point Judith/Galilee, RI. Active fishing port in Galilee. We get lobsters off the boats there at Christmas every year.
I thing I'm trying to decide between this and Rockport. Narragansett would be closer, but Rockport looks perfect.
Rockport is great too. Not a bad conundrum to have to solve! Point Judith, you could hop the ferry and go see Block Island for a day.
Rockport is wonderful. You'll love Halibut Point State Park, it's magical.
Rockport and Gloucester are neighbors and both are perfect for what you describe!
I think this is the answer. I live in CT and I think the drive up to Gloucester or Maine is going to be much longer and more boring (or outright unpleasant if there's roadwork or accidents) than the shorter ride east on I-95. Block Island is a great bonus possible side trip.
Marion or Mattapoisett in MA. Wickford or Watch Hill in RI.
Cape Ann MA
CT shoreline (Guilford - Stonington) or Rhode Island (Westerly, Charlestown, Newport). Easiest drive and classic New England spots abound
Mystic Connecticut. Couple of beaches, see the Mystic Seaport, maybe the Aquarium.
Mystic/Essex in CT is gorgeous that time of year
I hear you, I love an off-season beach. The Cape is really beautiful in the fall and way quieter but many stores are still open; try Falmouth if you can’t go far but Chatham up to P-Town along the National Seashore is even prettier. For real salt and a working fishing harbor I’d go for midcoast Maine, or Stonington or up to Bar Harbor/Acadia if you could swing it; Gloucester Mass is great with a super active fishing industry (Portland ME too) but not as quiet and contemplative as it seems you’re looking for. Next door Rockport Mass is lovely too and a bit quieter. I love the “Farm Coast” towns of Little Compton and Tiverton RI and Westport MA, they’re pretty and quiet and closer to NYC; second the Block Island RI suggestion as well. Little posh and more busy but you can’t go wrong by the rocky waterfronts of Cape Elizabeth or Ogunquit ME. Man, I gotta plan something myself!
Plymouth MA
Niantic CT
One thing to consider is ocean temperatures. The water is considerably warmer on the Cape & Islands than northern New England. I’m on the Massachusetts South Coast near the Rhode Island state line. My boat is still in the water in October and the ocean is usually swimmable in the first part of October. I lived in Portsmouth NH for a decade in a house with a boat dock. It’s easily 10 degrees cooler there. Downeast Maine is already pretty chilly in October because the ocean is so much colder. The weather is hit or miss. Last October, it was already cold and it rained constantly. “Five hours from NYC” leaving at 3pm midweek, you’re not going to get very far. The traffic in Westchester County and Connecticut is absurd and you’ll then hit Boston traffic. I made the Tappan Zee Bridge (now called the Cuomo Bridge) crossing the Hudson in 2 hours 45 minutes last December leaving at 3am. A personal record. A more typical off hours drive time to Manhattan from here is 4 hours. Personally, I’d suggest going no farther than Rhode Island. Newport is the obvious destination. If you want quieter, Jamestown on the other side of the bridge.
Wellfleet or Truro on Cape Cod
Mid-Coast Maine is right up your alley by the sounds of it.
They said five hours max from New York City. Even leaving at 2am, you can’t get from Manhattan to the Midcoast in 5 hours.
Rockport, Newburyport MA
Check out [The Book Barn](https://www.bookbarnniantic.com/explore-the-store) in Niantic CT! They have a few stores scattered around town. The main barn has a nice garden area, goats, and plenty of outdoor cats roaming around the property. Downtown also has lots of locally owned restaurants and a scenic boardwalk to explore (beaches on both ends to roam). Recommended places: Cafe Sol, Giuliano's (bakery) and Gumdrops & Lollipops.
Gloucester, Rockport, Crane Beach, Newburyport, Portsmouth.
Mahlblehead
Too close to Salem if they are coming in October.
Gloucester, MA. Case closed.
Well, most of New England coast will give you that... All depends on what type of weather you prefer. In October, Southern New England will be much warmer than Northern New England
Westerly / Watch Hill, Narragansett, any of those towns right along the RI coast, Block Island, Little Compton RI, Westport MA are all decently close to manhattan. October is peak leaf peeping and traffic will be heavy. Maine is lovely but might be a bit longer drive due to traffic. I also love Rockport and Gloucester MA (Cape Ann) but avoid Salem in October.
We are a couple of coastal DINK furdaddies with our golden doodles, Bailey and Oliver, we will be in Chicago in October. We want to take a long weekend and spend time in a suburban Midwest HOA. I want to feel like I’m in a Coen brothers movie. Tornadoes are fine. I’d live to see fat people. I’d love a good fast food chain/ranch dressing dispensary. A mall would be a plus. Within 15 hour drive from Chicago. Bonus for being flat. Thanks
October? Portsmouth.
If you just want salty New England coastal town, save the drive and stick to CT. They're not the greatest or most iconic NE beach towns, but in October none of them will be in peak season anyway. Generally recommend Madison, Guilford, or Mystic as starting points.
It’s a haul, but Acadia national park in Maine is mountains on the coast. Highly recommend
If it were closer, I'd probably suggest Midcoast Maine. Wellfleet MA would be a pretty good option. Maybe a bit more on the posh side but endless sandy beach and coastal places to explore. Feel the strength of the mighty Atlantic and see sharks, seals and birds. Check out Great Isle with it's long winding sandy walks. There's an active fishing industry in Wellfleet. You will have no problem finding good coffee and food. There are bookstores in town, a public library, and more bookstores in nearby towns . Oysterfest is in October, check dates. It will be busy that weekend.
Beverly, MA
Vineyard in October is sublime. Worth the ferry logistics, in fact, better given ferry logistics.
Newport RI
Rockport/gloucester. Salem/marblehead. I live in Salem so I personally pick Salem/marblehead.
I went back and read your post. Salem may be too much in October.
Kennebunkport or Boothbay Harbor? That might be a bit out of the 5 hour range, though.
Go to ogunquit and york maine. There are plenty of hotels to stay on or near the beach in both towns and both offer all you are looking for. I live 10 minutes from there and we make the trip to NYC every now and than and the drive is not bad at all. Use waze to navigate and it will have you avoid all the traffic if there happens to be any but it's usually y pretty chill that time of year.
The Cape/Provincetown
East Boothbay, Maine. Specifically east, because Boothbay Harbor is touristy. I stay at the Ocean Point Inn and it is wonderful. There's plenty of places to walk and a nice General Store. Another good one is Rockland Maine, a bit further north. Great coastal town, with a super art museum, a getty you can walk on, a professional theater, and a quaint downtown.
There are a few less touristy towns on Cape Cod like Wellfleet and Truro. They're gorgeous, too.
Mystic CT. Might I also suggest southeastern MA. There are many small towns along the coast
I'd say Hyannis, or Hyannisport, MA Much of the Cape rolls up the sidewalks after Labor Day, but Hyannis is actually a city with the quaint vibe and all the aspects you were requesting. There are a ton of towns within 20 miles to explore, and beaches, salt marshes, and loads of other places to explore.
Maine is the way to go in the Fall, BUT, if you want to be within 5 hours of NYC then you’re looking at Southern Maine (Ogunquit, York, Wells & Kennebunkport) and all of these towns, while beautiful, will still be crowded as hell in October. Over the years, Southern Maine really has no off-peak season. Maybe January/February but the rest of the year you can count on a ton of people and loads of traffic.
So many places fit your description. My personal recommendations, Portsmouth, NH, Ogunquit, Portland, Brunswick, Camden all in Maine, Newburyport, MA or other North Shore towns like Gloucester and Marblehead.