Home » Destinations » The Ultimate New England Bucket List

The Ultimate New England Bucket List

Hi everyone! Today’s post is going to cover all things New England! Being Boston-born & raised, all of New England feels like home to me. From summers swimming along the Maine coast to beach walks in Rhode Island to autumn hikes in New Hampshire to ski days in Vermont to college fun in Fairfield, Connecticut, I traverse New England often. Growing up in New England has allowed me to see so much. Each of the states offers unique scenery and activities, and are all within driving distance of one another. If you’ve never been to New England, I highly recommend visiting a few of the states during a road trip! And if you have been, or even live in one of these states, I hope this New England bucket list provides you with some new trip ideas!

This post contains affiliate links. If you click and book through any of these links, I will earn a small commission at no additional cost to you. Thank you so much for reading and supporting my little corner of the internet!

About New England…

New England is the northeastern region of the United States comprising of 6 states: Maine, New Hampshire, Vermont, Massachusetts, Connecticut, and Rhode Island. These states are some of the oldest in the United States and are known for their Colonial past. Also, the states of Maine, New Hampshire, Massachusetts, Rhode Island, and Connecticut are known for their Atlantic Ocean coastlines. New Hampshire and Vermont are known for their mountain ranges and fall leaf peeping. Boston, the capital of Massachusetts, is the largest city in New England and is known for its history and Instagrammable places!

Disclaimer: This list doesn’t cover all of New England’s sights, just my personal recommendations! Let’s jump into the New England bucket list!

State #1: Maine

Ahhhh beautiful Maine! Maine is known for its charming coastal towns in the south, Acadia National Park in the north, and a whole lot of lakes everywhere else. Maine is the largest state in New England and borders Canada in several places. I recommend visiting southern Maine and sightseeing the towns and lighthouses along the coast. Oh, and don’t leave without eating a lobster roll!

1. Acadia National Park & Bar Harbor

I recently visited Acadia National Park this August and loved it! Bar Harbor is located about 4 hours north of Boston and is the “gateway to Acadia”. If camping in the park isn’t your thing, check out the quaint hotels and restaurants located here instead! I recommend staying in the Bar Harbor Manor. It’s in a great location and so charming. 

While in Acadia, be sure to watch the sunrise from the top of Cadillac mountain. Acadia gets the first sunrise in US each morning, so don’t miss it! As for hiking, I recommend the Beehive trail. It’s super fun to climb, and you’ll get the best views of Sandy Beach from the top! Overall, my number one recommendation is to visit Jordan’s Pond House for a picnic! The scenery here was my favorite in the park and the popovers and blueberry tea were to die for.

Pro-tip: Not into hiking? This Narrated Bus Tour of Bar Harbor and Acadia is the perfect way to see the highlights of the area from the comfort of a seat! If it is rainy during your visit, this is the best way to see the sights. 

Sunrise from the top of Cadillac Mountain in Acadia National Park, Maine
Beehive Trail in Acadia National Park, Maine
Jordon Pond in Acadia National Park, Maine

2. Visit Portland

Portland’s Old Port waterfront has tons of shops and restaurants to check out. If you’re over the age of 21, spend the day at one of Portland’s several breweries! I also recommend seeing the Portland Head Lighthouse.

Portland Head Lighthouse

3. Ogunquit & Marginal Way

One of my favorite coastal towns in Maine! If you’re looking for an activity to do here, check out Marginal Way, a one-mile coastal walk with several benches along the way for enjoying the scenery!

Pro-tip: Feeling hungry? Head to Loveshack Juicery for a smoothie or açaí bowl… they’re delicious!

Marginal Way in Ogunquit, Maine on the New England Bucket List
Ogunquit, Maine on the New England Bucket List
Loveshack Juicers in New England

4. Kennebunkport

Another charming coastal town in southern Maine! Check out Dock Square for shopping, dining, art galleries, and more. Also, take a historic trolley ride for some sightseeing and a visit to the Bush family compound. If you’re visiting from Boston, this Maine Coast day-tour also includes a trolley ride of the town!

Visiting in the winter? Add Kennebunkport’s annual Christmas Prelude to your New England bucket list!

Kennybunkport, Maine
Maine during the holidays should be on your New England bucket list

5. Shop At The Kittery Outlets

Located right across the Maine border from New Hampshire, Kittery is famous for its shopping outlets. Here’s a store directory. Happy shopping! Also, check out nearby Fort Foster Park for a fun beach day!

Kittery Outlets in Maine
Pier at Fort Foster in Kittery, ME

6. Old Orchard Beach

One of the tourist “hot-spots” in Maine. Besides the beach, there’s a fun boardwalk and amusement park!

Pro-tip: There’s fireworks here every Thursday night in the summer!

Fun at Old Orchard Beach in Maine!

7. Nubble Lighthouse In Cape Neddick

Probably the most well-known lighthouse in Maine. It was put into use in 1879 after Congress funded its build and is still in use today.

You can drive to the lighthouse by plugging this address into your GPS: Sohier Park Rd, York, ME 03909

Pro-tip: Traveling with young children? Check out nearby York’s Wild Kingdom!

Nubble Lighthouse in Cape Neddick

State #2: New Hampshire

New Hampshire really has it all! The Atlantic coastline, charming historic towns, mountains, lakes, ski resorts, and even indoor waterparks. I spend most of my time in mid-New Hampshire, about two hours north of Boston, where most of the lakes and ski resorts are located. Growing up, we had a home near Mount Sunapee in Grantham, New Hampshire, close to Dartmouth College where my dad and grandad went to school. I love hiking in this area and highly recommend visiting the mountains in September or October when the fall foliage is at its peak.

1. Portsmouth

A quaint, historic coastal city in New Hampshire with more restaurant seats than residents! Yup, Portsmouth has more restaurants per square mile than they do people! This city has a booming arts district and also happens to be my family’s new hometown!

Portsmouth, New Hampshire during the holidays

2. Lake Winnipesaukee

Lake Winnipesaukee is huge. It’s the largest lake in New Hampshire and is located in the Lakes Region of the state in the White Mountains. There are several towns that border the lake, but I recommend visiting Wolfeboro, Laconia, or Meredith and checking out their charming harbors.

Pro-tip: Lake Winni is best explored by boat. Rent one for the day if you don’t own one!

Lake Winnipesaukee at sunset
Meredith, NH needs to be on your New England bucket list

3. Ski The White Mountains

New Hampshire is home to several fantastic ski resorts in New England, including Bretton Woods, Loon, and Cannon — all of which happen to be situated in the White Mountains.

Doable in a day trip from the Boston area, get up early and hit the slopes! Avoid weekends and school breaks if you can, as most New Englanders flood the mountains then.

Ski the East

4. Visit The Ice Castles

Ice Castles are located in Colorado, Utah, Wisconsin, Minnesota, Canada, and New Hampshire. The ones in New Hampshire are located in Woodstock, NH and are open seasonally from January-March each year (weather permitting). Fun to explore for all ages, here’s the website to learn more!

Pro-tip: Reserve tickets online and in advance for this activity! Time slots tend to book up fast.

The Ice Castles in New Hampshire

5. Mount Washington Resort

Located near Bretton Woods and the Mt. Washington Cog Railway, the Omni Mount Washington Hotel is a stunning place to stay year-round.

Mount Washington Omni Resort

6. Franconia Notch State Park

Some friends and I camped here a few summers ago and had a blast checking out the various trails and waterfalls located within this state park. Also located within the White Mountains, I recommend starting your trip at the Visitor’s Center to collect a trail map and check out Flume Gorge.

Flume Gorge in NH needs to be on your New England bucket list
Flume Gorge in NH needs to be on your New England bucket list

7. Drive Along The Kancamagus Highway (Route 112)

Known as the best scenic drive, this highway needs to be added to your New England bucket list! It runs laterally through northern New Hampshire and is 56 miles long. Be aware of windy turns at times, but enjoy the beautiful scenery — especially in autumn when you can leaf peep!

Leaf peeping in northern New Hampshire in autumn
Leaf peeping in northern New Hampshire in autumn
Leaf peeping in northern New Hampshire in autumn

8. North Conway

North Conway is the center of year-round northern New Hampshire activities. Located at the base of the White Mountains, North Conway is the perfect destination for a fall hiking trip or winter ski trip in New England.

In North Conway you will find the Settler’s Green Outlet Village, an indoor waterpark at the Red Jacket Mountain View Resort, and the Conway Scenic Railroad.

9. Swim In Diana’s Baths

Also located in the White Mountains and easily accessible from North Conway, Diana’s Baths is a hot-spot for tourists and New Englanders alike in the summer months. The small waterfalls found here are perfect for swimming, especially for kids.

Pro-tip: Here’s the address to reach the falls: 3725 West Side Rd, Bartlett, NH 03812

Swimming in Diana's Baths in NH should be on your New England bucket list

10. Hike Mt. Major Or Rattlesnake Mountain

There are countless hikes to do in New Hampshire, but the reason why I recommend these ones is because there is little work for a great reward! Both hikes take about 30 minutes to reach the summit and are less than 3 miles roundtrip. Both are located in the Lakes Region and have some of the best summit views in the state!

New England Bucket List hike

11. Fruit Picking At Applecrest Farm Orchards

Check out Applecrest Farm located in Hampton Falls, NH. This place is super cute and has several PYO offerings for each season. This summer I picked strawberries (July) and blueberries (August). This fall, they’re offering pick your own pumpkins, apples, and raspberries, so add this place to your fall New England bucket list!

New England Bucket List fruit picking
New England Bucket List fruit picking

12. Stay In A Getaway House

I did this recently with my sister and dogs (lol sibling trip) and couldn’t recommend it more! Located in Epsom, NH about one hour north of Boston, this was the perfect local escape I never knew I needed. Getaway homes are tiny houses located across the USA that encourage you to disconnect with devices, and to connect with nature and your loved ones. You can read more about Getaway House by reading this blog post!

Staying in a Getaway House in New Hampshire

State #3: Vermont

I love Vermont. It’s such a nice getaway from the hustle and bustle of Greater Boston. Vermont is also known for its mountains — I recommend hiking and skiing the Green Mountains and spending a fall or winter weekend away in one of the Vermont’s charming towns. I recently visited Woodstock and fell in love with its covered bridges and quaint cafes. Northern Vermont is home to Lake Champlain and Burlington, VT. My cousins both went to UVM, so I’ve been to Burlington a few times and highly recommend it!

1. Quechee Gorge

I recently took a day trip to VT and couldn’t recommend a visit here enough. Park at the Visitor’s Center and follow the trail through the woods down the side of the gorge until you reach the bottom. Check out the rocks here — many people swim in the summer months!

Quechee Gorge in Vermont

2. Visit Woodstock

Woodstock is one of the most charming towns I’ve ever been to. Known for its countless covered bridges, I recommend visiting in the summer or fall. Don’t forget your camera!

One of Woodstock, VT's several covered bridges
Woodstock, Vermont in the fall

3. Burlington & Lake Champlain

Burlington is one of Vermont’s most northern cities (about 4 hours from Boston) and is home to UVM! I recommend pit-stopping in Burlington if you’re road tripping to Canada from the Boston-area. My boyfriend and I did this on our way back from a weekend in Montreal!

Burlington’s lake front is lovely to bike along in the summer months, and so is a stroll down Church Street — Burlington’s downtown, pedestrian-only area. Here you’ll find tons of shops, restaurants, and Ben & Jerry’s of course!

4. Fall/Winter Weekend In Stowe

Also located about 4 hours north of Boston is Stowe, VT! Stowe is the perfect place for a winter weekend getaway and should definitely be added to your New England bucket list. I recommend checking out the Lodge at Stowe Mountain Resort if you like to ski and visiting the area in the fall if you like to hike.

Von Trapp Lodge in Stowe, VT
Stowe should be on your New England bucket list
Stowe, VT in October

5. Ski At Killington

Killington Ski Area is the largest ski mountain in the eastern United States and is known as the “Beast of the East”. If you can’t make it out west of ski season, brave the slopes at this popular ski resort in New England!

Ski resort on New England bucket list

6. Tour The Ben & Jerry’s Factory

Located in Waterbury, VT, this factory was the first one Ben & Jerry’s ever operated. Today, you can tour the factory and sample countless flavors.

Ben & Jerry's factory in Vermont

State #4: Massachusetts

Massachusetts is the hub of New England activity and is the most populated state in the region. Most of MA is full of suburban neighborhoods, but there is so much to see! Outside of Boston’s sightseeing and sports teams, there’s Cape Cod and the Islands, Cape Ann (Rockport & Gloucester), spooky Salem, and the Berkshires in western Massachusetts.

1. Boston

I think this one is pretty self-explanatory. Maybe I’m just biased, but everyone should visit Boston in their lifetime. I have a full blog post on the most Instagrammable places in Boston, but here are the bucket list highlights:

  • Red Sox game at Fenway Park (and be sure to order a Fenway Frank)
  • Shop in Faneuil Hall & grab a bite to eat in the Quincy Market
  • Italian dinner in the North End (don’t forget to grab a treat at Mike’s Pastry afterwards)
  • Walk the Freedom Trail to learn all about American Revolutionary history
  • Stroll through picturesque Beacon Hill (Acorn Street in particular for photos)
  • Enjoy the Boston Common & the Public Garden
  • Shop on Newbury Street
Red Sox game at Fenway Park in Boston, MA
A snowy day in Boston's Public Garden
Strolling down Acorn Street in Beacon Hill
Boston's Seaport District
Museums in Boston on a New England bucket list

2. Visit Minuteman National Historical Park

Located in Lexington and Concord, Minuteman National Park is the site of America’s Revolutionary War! Reenactments occur here often along with frequent historical tours. The historical battle trail that runs through the park is 5 miles long and is great for walking or biking!

Minute Man National Historic Park in Boston

Pro-tip: Looking for something more active? Check out the Minuteman Bikeway, a 10-mile paved path passing through the towns of Bedford, Lexington, Arlington, and Cambridge.

Mile 10 of the Minuteman Bikeway in Bedford, MA

3. Cape Cod & The Islands

A trip down the Cape is a can’t-miss New England bucket list item. If you’re unfamiliar, the Cape is the “arm” of Massachusetts and consists of well-known vacation towns such as Falmouth, Chatham (where the Great Whites are spotted every summer!), Wellfleet, and Provincetown, or P-Town. P-Town is the very tip of the “arm” and is known for its artists and thriving LGBTQ+ community! This post covers how to spend a day in Provincetown if you’re interested in learning more!

The Massachusetts islands are Martha’s Vineyard and Nantucket. In Martha’s Vineyard you have to explore Oak Bluffs and the famous carousel there. Also, I recommend jumping off the Jaws bridge in Edgartown if you’re feeling adventurous and splashing in the giant waves at Katama/South beach if you’re feeling even more adventurous. You can visit Martha’s Vineyard by taking a ferry and full-day tour from Boston!

I’ve only been to Nantucket a few times. It’s smaller than Martha’s Vineyard, but is equally as luxurious. The downtown of Nantucket is famous for its wharf, cobblestone streets, and high-end boutiques. Both Nantucket and Martha’s Vineyard made my list of the top girls weekend getaways in the US Northeast!

Visiting Cape Cod in Massachusetts
Beach in Borne, Cape Cod, MA
Add Nantucket to your New England bucket list
Vineyard Vines in Martha's Vineyard
Jaws Bridge in Edgartown, Martha's Vineyard
Gingerbread Houses in Oak Bluffs, Martha's Vineyard

4. Rockport

Rockport is located in northeast Massachusetts in a region known as Cape Ann. This is also where you’ll find the coastal towns of Gloucester, Manchester-by-the-Sea, and Essex!

Rockport is one of my favorite places to visit for a day trip. I recommend spending the day exploring the sea rocks at Halibut Point State Park (dog friendly!) and then hitting the downtown for a seafood lunch and some shopping! Check out nearby Good Harbor and Long Beach if you’re interested in a beach day, but be sure to arrive early — the parking lots here fill up fast!

The ultimate New England bucket list

Rockport, MA should be on your New England bucket list

5. Visit Salem In October

Salem is magical year-round, but visiting spooky Salem in October really is an experience. Famous for its 1692 witch trials, in which several locals were publicly executed for believed practice of witchcraft, Salem is fun to explore. Downtown Salem also has several charming shops and restaurants. My favorite is the Ugly Mug Diner for brunch!

Pro-tip: This Salem History and Ghost Walking Tour is the top-ranked tour in the area and is the perfect way to see the highlights. 

Downtown Salem, MA in October
Downtown Salem, MA in October

6. The Berkshires

The Berkshires is the region in the far west of Massachusetts known for its B&B’s, art community, farm-to-table food scene, and outdoor activities. A visit to the Berkshires is best in the fall when the region is the most scenic, especially in Northampton, where you’ll find UMass Amherst, a charming downtown, and some of the best fall views in MA! I also recommend visiting the Quabbin Reservoir in western Massachusetts. Not only does it supply most of Mass’s water, but it’s a beautiful place to hike!

Pro-tip: Feeling crafty? Check out Snow Farm, an art school in Williamsburg, MA. My mom and I have taken several art classes here, including painting and pottery!

Visiting the Berkshires in the fall needs to be on your ultimate New England bucket list
Bear's Den Hike near the Quabbin in Western MA

7. The Quincy Quarries & Mary Lou’s

Spend some time exploring Quincy’s quarries! This area is known for its skyline views of Boston and famous graffiti art. Since you’re near the south shore, head on over to a local Mary Lou’s for some of the best coffee you’ll ever have!

Quincy Quarries in Boston, MA
Marylous is a must on a New England bucket list

8. Colby Farm

Located in Newbury, Colby Farm is the place to be from late August to mid-October! For about three weeks, they have one of the only sunflower fields in New England, so if you’re looking for some cute pics, add this place to your New England bucket list! I went this year the first week of September, and thank goodness I did because they closed right after Labor Day. In the fall this place has an awesome farm stand.

Sunflower field in New England

9. Visit Plymouth

I think every American should visit Plymouth once in their lifetime. It’s where the pilgrims first landed on the Mayflower in 1620 and is known as “America’s Hometown”. Spend a few hours exploring Plimoth Patuxet, previously known as the Plymouth Plantation, before heading to downtown Plymouth to see the Mayflower II, the Plymouth Rock, and for some yummy seafood!

Pro-tip: You can buy tickets to all of the attractions online. This ticket will grant you access into all the sights mentioned above, plus more!

Plymouth Plantation is a must for a fall New England bucket list
Plymouth Plantation is a must for a fall New England bucket list
Plymouth Plantation is a must for a fall New England bucket list

State #5: Rhode Island

Rhode Island is the smallest state in New England and has a beautiful southern coast, where you will find the Narragansett beaches and Newport. Newport is one of my favorite getaway spots on this New England bucket list — don’t miss it! Providence, the capital, is full of well-known college campuses and Federal Hill, the charming Italian district. Although small, don’t skip over this state!

1. Newport

My favorite place in Rhode Island! Newport is home to the Cliff Walk, a 3-mile coastal walk which passes Newport’s famous Breaker mansions. If you want to explore this area, I recommend parking on Salve Regina’s campus for the walk!

Although summer is the best time to explore Newport’s coast and charming downtown (GREAT shopping!), check out the Breakers Mansion around Christmastime! The mansions are decorated beautifully for the holiday season and holiday-themed tours are offered annually.

Newport Mansions in Rhode Island
Breakers Mansion in Newport, RI
View from the Cliff Walk in Newport, RI

2. Block Island

It’s easy to access Block Island by ferry from the Narragansett area in southern Rhode Island. The ferry ride is about an hour and will bring you right to the charming downtown. My friend Matt and I explored some of the shops downtown and rented bikes — the preferred method of exploring the island!

We biked all around Block Island, with the highlights being visits to the Southeast Lighthouse and Mohegan Bluffs. Mohegan Bluffs are giant cliffs with a picturesque staircase that descends down to one of Block Island’s most popular beaches. Don’t leave the island without snapping a photo here!

Mohegan Bluffs on Block Island, RI
Mohegan Bluffs on Block Island, RI

3. Wicked Tulips Flower Farm

I think this is one of the lesser known ideas on this New England bucket list, but I promise you won’t want to miss it.

Located in Exeter, Rhode Island, this tulip farm is open annually each spring and allows visitors to hand-pick tulips to bring home. They provide you with the cutest wicker baskets and allow you to pick 10 flowers to bring home. Not only did my family and I get the best photos here, but the tulips here are STUNNING. Rows after rows of them, just like there are in the Netherlands, right here in Rhode Island. Check it out!

Wicked Tulips Flower Farm in Rhode Island

4. Federal Hill In Providence

Providence is the capital of Rhode Island and has a lot to offer. From the WaterFire event each summer to the giant Providence Place Mall to Brown & PC, there’s a lot going on.

My favorite area in Providence is the quaint, Italian district called Federal Hill. I recommend Costantino’s for authentic Italian cuisine!

5. Ride With Rail Explorers

After seeing this on TikTok back in the spring, I knew I had to give this a try. Located in scenic Portsmouth, RI, Rail Explorers has you peddle your own vehicle through 3-miles of coastal track. The best part? The halfway spot is at an outdoor bar and picnic area. Check it out!

Pro-tip: Not in New England? You can also ride the rails in New York and Las Vegas!

Riding with Rail Explorers
Riding with Rail Explorers needs to be on your New England bucket list

6. Watch Hill

Home to the one and only Taylor Swift, this affluent coastal town is located in Westerly, RI. The beaches here are stunning, the downtown is super cute, and the homes are HGTV-worthy. My favorite area here was the Ocean House, a historic Rhode Island beach hotel. It’s pricey, so we just came here for dinner and YUM — couldn’t recommend it more!

Ocean House in Rhode Island

State #6: Connecticut

And finally, this brings us Connecticut! Connecticut’s capital is Hartford, and although it’s not my favorite city, Connecticut has several charming towns that I recommend visiting. The Atlantic coast has towns such as Old Saybrook and Mystic. As you drive along 95 into southern Connecticut, you’ll hit Fairfield. I’ve spent the past four years of my life living here for college, so it has a special place in my heart. Maybe I’m just biased, but I do think Fairfield county is worth the visit, especially to see towns like Westport and Greenwich, two of the wealthiest places in the US.

1. Old Saybrook

Located in southern Connecticut at the mouth of the Connecticut river, Old Saybrook is a charming coastal town with an eclectic downtown and stunning lighthouse.

2. Mystic

Another charming coastal Connecticut town with an historical downtown, several dining options, and an aquarium! This area was once a significant Connecticut seaport and has an interesting boating history. Check out the Mystic Village if you feel like shopping.

Pro-tip: Feeling hungry? Don’t leave Mystic without trying Mystic Pizza! There was a famous movie filmed here and it’s seriously the best I’ve ever had.

Add a day trip to Mystic, CT to your New England bucket list
Cider Mill in Mystic, Connecticut

3. Explore Fairfield County

This New England bucket list item is totally biased since I went to Fairfield University inConnecticut for undergrad, but I think Fairfield county really is worth the visit.

Not only does the town of Fairfield have the BEST restaurants I’ve ever been to, but Fairfield county is also home to the picturesque towns of Greenwich, Southport, and Westport.

If you watch your fair share of HGTV like I do, you will definitely want to take a drive through some of Greenwich’s neighborhoods and admire the luxurious downtown of Westport, CT.

Fayerweather Island Light in Bridgeport, CT in Fairfield County
Sasco Hill Beach in Fairfield, CT
Jennings Beach in Fairfield, CT

4. Shops At Yale In New Haven

New Haven is a fun city to hangout in because of its high population of students! There are several universities in the area, with the most well-known probably being Yale. The Shops at Yale are a nice part of the city to hangout in.

That’s all for my New England bucket list! I hope you all got some new ideas from this list and check out some of these places soon. Since New England is fairly small, it’s easy to see a lot. Fill up your gas tank, grab a friend, hit the road, and cross a few more sights (and states) off your New England bucket list!

Like this post? Pin it to save it for later and share with others!

New England Bucket List pin


  1. Grace
    June 3, 2020 / 1:50 AM

    I found your blog from the Gals on the Go Facebook Groupchat and I have to say, I am in LOVE with it. You have inspired me to want to get out and explore! This is truly an amazing website and you deserve so much credit for all the hard work you put into it. As a Rhode Islander, it is especially exciting to see people post about the state and it’s hidden beauties. It truly is underrated! Keep up the great work and I can’t wait to see where you travel to next!

  2. June 5, 2020 / 8:47 PM

    Hi Grace, thank you so so much for the kind words! This comment means a lot 🙂

Leave a Reply

Your email address will not be published. Required fields are marked *

Looking for Something?