New England (and New York) Fall Road Trip - Must See Sights

Once September hits in New England, I start planning my favorite getaways. Days spent hiking, evenings spent camping, nights in cozy cabins and morning in the crisp New England Air. Leaf peeping and scenic drives, apple picking and fairs - all the good things we are so ready for after a toasty humid New England summer.

Last month, someone asked for some advice on planning a fall New England road trip and I was embarrassed to admit that post didn't exist yet. I quickly got to work, going state by state to share some of my favorite places in the northeast.

Waterville Valley Ski Resort/Mount Tecumseh

Hiking Vermont's Tallest Peak, Mount Mansfield

This guide is a "pick your party" kind of adventure. I categorized my favorite fall things by state and put a double asterisk (**) by the things you should not skip. If you are a native New Englander, you can plan a series of day trips or weekend getaways, chasing fall through the area. If you are traveling from outside the northeast, you can pick a favorite or two from each state depending on how much time you have, and plan an epic road trip. 

Start in Northern New York or Vermont in late September and work your way down New England, targeting peak foliage as September and October pass us by. This Peak Foliage Map is vital in planning on when to visit where.

Waterville Valley Ski Resort/Mount Tecumseh

Click around and use this interactive map to plan your ultimate New England Fall Road Trip. Plan on September 22nd ish for the start of peak foliage in the northern parts of New Hampshire, Vermont, and Maine. The end of September and early October marks peak foliage for the central parts of these states. Connect, Rhode Island and Massachusetts won't see peak foliage until the second week of October. If you are adding on New York to your New England road trip, then this order of states forms a perfect circuit (with my must-see sights).

• Adirondacks, New York: Lake Placid Area (The Wild Center, Indian Head Hike, Lake Placid/Mirror Lake)
• Northern Vermont: Stowe, Kingdom Trails/Burke, 
• Northern New Hampshire: White Mountain Region, Kancamagus Highway
• Southern Maine: Portland (Old Port, breweries/restaurants)
• Southern New Hampshire: Portsmouth 
• NE Massachusetts: Salem/Gloucester/Rockport 
• Southern Rhode Island: Newport (mansions, wharf, Cliff Walk)
• NW Connecticut: Appalachian Trail/hiking, Kent
• Catskills, New York: Hiking 

Kingdom Trails, East Burke, Vermont

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Vermont is probably the first state that comes to mind when you think of "Fall in New England". I am here to tell you that yes, it's as gorgeous as everyone hypes it up to be and it's certainly one of my favorite spots to head to. Expect for the foliage in northern Vermont to peak early (September 22ish and on). 

** Kingdom Trails/Burke: We usually timed our Vermont Fall trip with a trip to Burke, Vermont to mountain bike Kingdom Trails. We often stayed at Burke Campground and spent the perfect fall days biking Kingdom Trails. It is a mountain biking mecca and so far, my favorite trail system here in New England. The town of Burke is also quite quaint, filled with cute restaurants, idyllic inns, rolling fields, and stunning fall foliage.  If you prefer to hike, you can also hike at KT or, head to Burke Ski Mountain to follow one of the trails up the ski mountain. 

** Stowe: Stowe, Vermont is a great option during any season but fall is something special. It's still nice enough to enjoy the patios at the local breweries and restaurants. You have a lot of great options for hikes (Stowe Pinnacle (3.2 miles), Sterling Pond (3 miles), Mount Hunger (4.5 miles), Bingham Falls (1/2 mile), Mount Mansfield (7 miles, highest peak in VT) 

Mt. Pisgah / Lake Willoughby: Also in the Northeast Kingdom, Lake Willoughby is the sort of place you find on a postcard. It's this scenic lake sandwiched between the mountains with hiking, biking, and xc skiing trails. 5 stars for foliage and a great place to hike. 

Burlington: Burlington on Lake Champlain is also a cute little city if you have time after Stowe. It's full of great food, great beer, walking and bike paths, famous Lake Champlain, and more. If the ferry is open, you can connect over to upstate New York/Adirondacks this way and really extend your road trip from New England and into New York.

Scenic View off Kancamagus Highway

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New Hampshire claims a close second to my favorite New England state in the fall. In the southern parts of New Hampshire, you can visit the coastal city of Portsmouth and stop into cideries and farms that celebrate fall. Up north, you have world-famous fall foliage drives and challenging hikes in the White Mountains. There is a hike for every skill level, accommodations for campers or spa-goers, and so many ways to see the mountain - on foot, on wheels, railway, or gondola.

**White Mountains Region: This is a special part of New England. The Whites are famous for their mountain peaks that are popular with hikers. Some of my favorite New Hampshire weekends were spent backpacking up in this area, enjoying quiet days in the backwoods of New Hampshire. The Whites are home to New England's tallest and most famous mountain, Mount Washington which you can visit on foot, by car, or by train (the famous cog railway). Mt. Tecumseh is the smallest of the famous 48 list (48 peaks over 4,000') and the foliage and views are amazing (you can hike the trail up and the ski mountain down). There is also a range of shorter and scenic hikes "52 with a view" is slower/steady and family-friendly is more your style. Lonesome Lake is the perfect scenic family-friendly hike that ends at one of New Hampshire's famous mountain huts. We stayed at Kinsmans Lodge bed and breakfast which was the perfect addition to a fall New England getaway. If you want to splurge, the Omni Mount Washington Resort is a famous hotel. There are a lot of great camping options up in the Whites if you really want to spend time in the mountains. 

**Kancamagus Highway: Another must-see (also up in the White Mountain region) is the Kancamagus Highway. This winding 35-mile two-lane road is a famous fall foliage drive that connects two famous New Hampshire towns. Lincoln is at one end and it's a cute little town with everything you could want in the fall including a skyride up Loon Mountain. The drive itself overs scenic vistas and overlooks, waterways, bridges, campgrounds, and a ton of hiking options.

Lakes Region: The lakes region of New Hampshire is also quite lovely. You can head to the Lake Winnipesaukee area and head out on the lake with your kayak or rent a boat. There are also a lot of great scenic hikes in the area, Mt. Major included.

Portsmouth: Southern New Hampshire is home to the cute little city of Portsmouth - this foodie haven is the perfect spot for walking around, shopping, and eating. You can find perfect little gems like Applecrest Farm, North Country Hard Cider, and take a nice walk at Odiorne Point.

Mt. Katahdin, Maine's highest peak

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Maine is the largest of the New England states. Here in Maine, you can find New England's only National Park, you can visit one of the biggest foodie cities in the country, and you can head deep into the woods of Maine to the terminus of the Appalachian Trail, far from cell service and "civilization".

**Portland, Maine: Portland is famous for its breweries and restaurant scene - you will find old cobblestone streets, harbor views, and the best food and beverages. It's one of my favorite New England cities and worth a visit. Get a lot of lobster dishes (like a lot) and enjoy the charm and eats in the city.

Acadia National Park /Bar Harbor: It's a haul up in the northern parts of Maine but it's our only National Park and it's an epic one. It's basically a National Park on an island and the kind of place where you don't have to pick hikes or oceans, you can have both. There are some AMAZING hikes (Beehive Trail and the Jordan Pond Loop are the perfect shorter hikes with the best views) and terrifying cliff-hanging style hikes like the Precipice Trail if that's more your style.

Kennebunkport and Ogunquit: These southern Maine towns are also perfect New England touristy towns and are easy to get to on the southern portion of Maine

Freedom Trail- Boston, Massachusetts

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While the northern New England states take all the marks for foliage, Massachusetts still has a lot to offer. Leaf peeping in the Berkshires gives you a getaway to small mountain tows without the crowds the northern New England states get. You also have the town of Salem which does Halloween like nowhere else in New England. You also have the chance to visit some of its popular islands (Martha's Vineyard and Nantucket in the off-season).

**Salem/Gloucester/Rockport: Salem, Massachusetts is home to the Salem Witch Trials, the famous trials in late 1600 where 19 men and women (mostly women) were accused of witchcraft and hung. The town goes bonkers for anything and everything Halloween. It gets a little crazy on fall weekends but it's certainly worth a stop to see the museums and events in the month of October. Gloucester/Rockport are darling little fishing towns adjacent to famous Salem, Massachusetts. Head here for a quieter scene where you can find fresh seafood and charming beaches.

Martha's Vineyard: Martha's Vineyard, typically quite busy in the summer months, slows down in the fall. If you have some warmer weather, it's a great place for a day trip, biking around the very bike-friendly island.

Boston: Boston is worth a visit if you love old cities and history. The Freedom Trail is a fun walk through the city, passing historic landmarks like Paul Revere's house, old burying grounds, churches, monuments, and Faneuil Hall.

Big E: If you find yourself in Massachusetts between September 17 and October 3 this year, then make a stop at the Big E in Springfield for an iconic New England fair. Every state is represented by it's own house where you can tour through and see a "glimpse" of what each state has to offer. If you are like me, you head to the Big E to spend the day eating to your hearts content. There are rides and exhibits, horse shows and oxen, it's something worth experiencing in the area. 

Jamestown, Rhode Island

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Rhode Island is small but mighty. I wouldn't come to Rhode Island for the leaf-peeping, but I would come for that coastal New England setting we all know and love.

** Newport cannot be missed! Newport is wonderful in any season but visiting in the fall means you can enjoy the nice weather without all of the summer traffic. It's the sweetest little ocean city home to the mansions you can tour! You can also walk along Cliff Walk - you will also find great shops and restaurants on the water.

Jamestown: Jamestown is always a quiet oasis if you prefer solitude, scenic biking, and spending time at historic state parks.

Block Island: The island deemed "Bermuda of the north" is worth the day trip if you don't mind a ferry ride. You can rent bikes and bike the island in a day. Not everything is open in October but if you have a nice day, it could be great.

Guilford, Connecticut

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I live on (and love) the Connecticut Shoreline but you will get a similar vibe from the coast of Rhode Island and Massachusetts. 

** Quiet Corner: While in Connecticut, I would head to the northeast corner where you can find awesome foliage, breweries, and hikes. Picture this scene: covered bridges, small towns, and you can even hike a portion of the famous Appalachian Trail. The towns in this area (Kent, Cornwall, Litchfield) are darling and have great options for eats. There are a ton of great hikes including Pine Knob Loop (Sharon), Rand's View (Canaan), Bear Mountain (Salisbury), and Macedonia Brook Loop (Kent). 

Indian Head Hike - Adirondacks, NY

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Okay, it's not New England but it's the northeast. We are going to break New York into two must-see sections, the northern part (Adirondacks) and more southern area (Catskills). 

The Adirondacks are farther north and offer bigger mountains and big lakes (incredibly scenic especially in the fall). Lake Placid was home to the Olympic games and is a great little spot in New York. This Weekender's Guide will give you an idea of some of the top attractions in the area (The Wild Center, Mountain Coaster at Mt. Van Hoevenberg). There are so many great hikes to choose from and Indian Head may have the best vista in the northeast. Jay Mountain and Ridge is also a great option. 

The Catskills are a quiet section of New York, south of the Adirondacks. This Weekender's Guide gives you a good idea of what to do in the area in a few days. The Catskills offer cute little mountain towns and great hikes. The Tiny House Resort is a pet-friendly fun place to stay (afternoon walk with the goats included). The Catskills has some great hiking including Giant Ledges, Overlook Mountain (fire tower and abandoned hotel ruins), Kaaterskill Falls (famous waterfall), North-South Lake/Newman's Ledge, and Whittenberg Mountain. 

Fall in New England cannot be beaten. It's the mix of amazing foliage in reds, oranges, yellows and golds. It's the quaint fairs and festivals, the small towns and the orchards. The weather is often warm and sunny by day and perfectly cool and crisp as the sun goes down. It's amazing camping weather and it's the best season in New England and it's much too short. I think you would need two weeks to do it justice, and a month would be even better. You can do a highlight reel in a week if you don't mind an aggressive schedule and a lot of driving. Don't forget to find some apple cider donuts and enjoy a cold pumpkin beer on tap. 

Happy Adventuring