5 Fantastic Fall Getaways in the Northeast

The crisp leaves, the chilly nights, the smell of a crackling fire, there is nothing quite like Fall.  It’s my favorite season of the year, and there is nowhere on this planet where fall is better than it is in the northeast.  Whether you’re looking for a little romance, or a fun weekend with friends, the fall in the Northeast has a little something for everyone. Here are five of our favorite fall getaways in the Northeast. Pack your bags!

Fall in Boston
Fall Leaves on the old streets of Beacon Hill in Boston


Boston’s a must-do for any fan of American History, but it really shines in the fall.  Students are back at one of the area’s 35 universities and the streets are bustling.  Boston is one of the nation’s most legendary sports towns, so if you’re a sports fan, taking in a Red Sox, Patriots, or college game can really set the stage.  

A stroll along the Freedom Trail will take you past many historical sites like the Old South Meeting House and Faneuil Hall.  No trip to Boston is complete without a little time on Boston Common watching the swan boats or if it’s cold enough, ice skating out on Frog Pond. 

Boston proper is fairly walkable, and the outlying areas like Cambridge are easily accessible by the city’s rail system, the T.  Staying at a hotel in Back Bay, like the Westin Copley Place or the grande-dame-esque Lenox Hotel will keep you easy walking distance to great restaurants and shopping along Boylston street and Commonwealth Ave and easy rail access to the Green, Purple and Orange Lines, as well as easy rail links to Logan Airport.

Bridge in the Catskills
Bear Mountain Bridge in Cortland, NY

The Catskills

Just 1-2 hours north of Manhattan, the rolling Catskills range in the Appalachian mountains provides a stunning and peaceful retreat from the hustle and bustle of the city.  The Catskills region is more about drinking in the nature than it is exploring shops and restaurants, but that doesn’t mean those can’t be a part of your trip.   

Charming villages and hamlets dot the area, each full of their own local restaurants and shops. Meander through the mountains and drink in the arts and culture in quaint towns like Woodstock, Livingstone Manor, Catskill, Saugerties, and Franklin. There’s a little something for everyone.

The Catskills are best experienced while staying in a Bed and Breakfast or small inn.  The Washington Irving Inn  near Hunter and Tannersville offers cozy accommodations amidst stunning mountain views.  The Onteora Mountain House in Saugerties is right on the doorstep of Woodstock, and gorgeous mountain views from private decks in many of the rooms.  

Looking for something that’s a little more of an event?  The Mohonk Mountain House is a fairy-tale castle nestled among the mountains with tons of activities and ultra luxe accommodations.

Boats in Bar Harbor in the Fall
Boats in Bar Harbor

Bar Harbor

The coast of Maine is unlike any other coastline in the world.  Bar Harbor is the nautical hub of this stunning corner of the country.  Classic New England coastal vibes meet the rugged shoreline in this charming town.

Aside from the charm of downtown Bar Harbor, the biggest draw here is proximity to Acadia National Park.  Take on Cadillac Mountain, or take a drive along the Park Loop Road, offering some of the best foliage viewing in the area.

Keep your eyes out for the Night Sky festival, usually held in late September, taking advantage of Acadia’s low level of light pollution, and see the inky night skies as you’ve never seen them before.

For a bit of luxury and romance, the Balance Rock Inn drips with classic Maine seaside elegance steps from the Shore Path The Black Friar Inn is another charming option with a fabulous location, just three minutes from the entrance to Acadia, full breakfasts, and a cozy pub to have a bite and a pint after a day exploring the area.

Canoeing in Fall in the Catskills, northeast fall getaway
Canoeing on Cayuga Lake

The Finger Lakes

The Finger Lakes region of Upstate New York stands about 4 hours from NYC, and about 5.5 from Boston, and while it’s generally known for it’s summer lake scene, the area has a TON to offer in the fall season, with lower crowds and, generally, prices.  

Aside from the famous upstate New York fall foliage, stunning lakes and the rolling mountains that surround them, the finger lakes offer a unique landscape, in a quieter locale, farther away from the more popular fall destinations.  

This area is chock full of old gilded-era estates retrofitted into small inns, which is, truly, the way to stay up there.  Places like Geneva on the Lake on Lake Seneca, Bellhurst Castle, also on Lake Seneca, The Brewster Inn in sleepy Cazenovia on Cazenovia Lake – all offer unique accommodations with million dollar views.

Keep your eyes out for the Vintage Grand Prix at Watkins Glen (held in early September, usually), for a once-in-a lifetime chance to see these impeccable vintage machines take to the track, and be sure to stop in at the Brae Loch Inn for dinner and a tipple from the largest selection of Single Malt Scotch in the region.

Fall Getaway on Cape Cod
Classic house in the dunes on Cape Cod

Cape Cod

Sure, you can go to the Cape in the summer with everyone else in the region.  Sit, frustrated at the bottleneck on Route 6, or cram yourself onto one of the ferries, OR, you can cruise up in September or October, and be able to enjoy what the area has to offer without the mobs of people, with crisp, cool nights, and hotel rates significantly lower than they are in peak season.

From whale watching out of Provincetown for a chance to see humpbacks in their natural habitat, to rolling down the Rail Trail from Dennis to Welfleet, there is no shortage of stuff to do in the fall on the Cape, all minus the crowds of peak season.  

Fall festivals are everywhere on the Cape, as well.  The Cape Cod Brew Fest, generally held in late September, will get you tastes of a TON of local and regional brews (including my personal favorite, Cisco Brewer’s Whale’s Tale Pale Ale – the lengths I go to get this out to me in my home base in the Rockies are pretty astounding).  The Wellfleet OysterFest is another classic event.  Cancelled in 2021, but keep an eye on it in future years.

AirBNBs and Vacation Rentals are common all over the cape, but don’t overlook the classic inns and guest houses of Cape Cod, like the Harbor View Hotel in Edgartown on Martha’s Vineyard, The Wequasset Resort and Golf Club , or the Chatham Wayside Inn.

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