3-Day Itineraries in Massachusetts

Long-weekend trips with every day mapped out — verified attractions, realistic pacing.

101 itineraries

Brick, Blade & Berbere: Three Days in Worcester

3 Days · Teen Families

Worcester, Massachusetts, Massachusetts

Brick, Blade & Berbere: Three Days in Worcester

9 stops

Brick, Blade, and Berbere: A Solo Wander Through Worcester

3 Days · Solo

Worcester, Massachusetts, Massachusetts

Brick, Blade, and Berbere: A Solo Wander Through Worcester

8 stops

Whimsy & Wonder: A Springfield Family Weekend in the Quadrangle

3 Days · Teen Families

Springfield area, Massachusetts

Whimsy & Wonder: A Springfield Family Weekend in the Quadrangle

6 stops

Whimsy and Wonder: A Solo Springfield Weekend

3 Days · Solo

Springfield area, Massachusetts

Whimsy and Wonder: A Solo Springfield Weekend

3 stops

Brick, Blade, and Berbere: Three Days Alone in Worcester

3 Days · Solo

Worcester, Massachusetts, Massachusetts

Brick, Blade, and Berbere: Three Days Alone in Worcester

10 stops

Brick, Blade & Berbere: A Worcester Weekend for the Whole Family

3 Days · Teen Families

Worcester, Massachusetts, Massachusetts

Brick, Blade & Berbere: A Worcester Weekend for the Whole Family

8 stops

Rock, Rope & Rising Tide: 3 Days in Plymouth

3 Days · Teen Families

Plymouth, Massachusetts

Rock, Rope & Rising Tide: 3 Days in Plymouth

10 stops

Stone, Salt, and Slate: 3 Days Alone in Plymouth

3 Days · Solo

Plymouth, Massachusetts

Stone, Salt, and Slate: 3 Days Alone in Plymouth

8 stops

Pond Light & Parlor Doors: 3 Days Alone in Concord

3 Days · Solo

Concord, Massachusetts

Pond Light & Parlor Doors: 3 Days Alone in Concord

5 stops

Little Women, Big Ideas: A Concord Family Weekend

3 Days · Teen Families

Concord, Massachusetts

Little Women, Big Ideas: A Concord Family Weekend

8 stops

Whimsy and Wonder: 3 Days in Springfield's Quadrangle

3 Days · Teen Families

Springfield area, Massachusetts

Whimsy and Wonder: 3 Days in Springfield's Quadrangle

4 stops

Whimsy and Wonder: A Solo Journey Through Springfield's Quadrangle

3 Days · Solo

Springfield area, Massachusetts

Whimsy and Wonder: A Solo Journey Through Springfield's Quadrangle

6 stops

Stone, Sail & Slate: 3 Days Alone in Plymouth

3 Days · Solo

Plymouth, Massachusetts

Stone, Sail & Slate: 3 Days Alone in Plymouth

8 stops

Revolution, Reflection & Red Leaves: 3 Days in Concord

3 Days · Teen Families

Concord, Massachusetts

Revolution, Reflection & Red Leaves: 3 Days in Concord

6 stops

Fallen Leaves & Transcendent Ground: 3 Days in Concord

3 Days · Solo

Concord, Massachusetts

Fallen Leaves & Transcendent Ground: 3 Days in Concord

8 stops

Rock, Rope, and Harbor Light: 3 Days in Plymouth

3 Days · Teen Families

Plymouth, Massachusetts

Rock, Rope, and Harbor Light: 3 Days in Plymouth

8 stops

Stone, Sail & Slate: Three Autumn Days in Plymouth

3 Days · Active Retirees

Plymouth, Massachusetts

Stone, Sail & Slate: Three Autumn Days in Plymouth

8 stops

Cobblestones & Quiet Mornings: 3 Days Along Boston's Freedom Trail

3 Days · Active Retirees

Boston Metro, Massachusetts

Cobblestones & Quiet Mornings: 3 Days Along Boston's Freedom Trail

6 stops

Museum Light and Quiet Streets: Three Days in Springfield

3 Days · Active Retirees

Springfield area, Massachusetts

Museum Light and Quiet Streets: Three Days in Springfield

5 stops

Brick, Bronze, and Autumn Light: 3 Days in Worcester

3 Days · Active Retirees

Worcester, Massachusetts, Massachusetts

Brick, Bronze, and Autumn Light: 3 Days in Worcester

6 stops

Autumn Light on Author's Ridge: 3 Days in Concord

3 Days · Active Retirees

Concord, Massachusetts

Autumn Light on Author's Ridge: 3 Days in Concord

5 stops

Brick, Bronze & Autumn Light: Three Days in Worcester

3 Days · Couples

Worcester, Massachusetts, Massachusetts

Brick, Bronze & Autumn Light: Three Days in Worcester

8 stops

Small Steps, Big History: 3 Days in Plymouth with Little Ones

3 Days · Young Families

Plymouth, Massachusetts

Small Steps, Big History: 3 Days in Plymouth with Little Ones

6 stops

Whimsy & Wonder: A Springfield Weekend for Two

3 Days · Couples

Springfield area, Massachusetts

Whimsy & Wonder: A Springfield Weekend for Two

7 stops

Rock, Rope Rigging & Harbor Light: 3 Days in Plymouth

3 Days · Couples

Plymouth, Massachusetts

Rock, Rope Rigging & Harbor Light: 3 Days in Plymouth

9 stops

Mill Bricks & Maple Light: 3 Family Days in Worcester

3 Days · Young Families

Worcester, Massachusetts, Massachusetts

Mill Bricks & Maple Light: 3 Family Days in Worcester

5 stops

Whimsy in the Quadrangle: A Slow-Paced Family Weekend in Springfield

3 Days · Young Families

Springfield area, Massachusetts

Whimsy in the Quadrangle: A Slow-Paced Family Weekend in Springfield

5 stops

Cobblestones & Small Steps: 3 Days of Revolutionary Boston for Little Legs

3 Days · Young Families

Boston Metro, Massachusetts

Cobblestones & Small Steps: 3 Days of Revolutionary Boston for Little Legs

6 stops

Falling Leaves & Transcendental Light: 3 Days in Concord

3 Days · Couples

Concord, Massachusetts

Falling Leaves & Transcendental Light: 3 Days in Concord

9 stops

Little Women & Loon Calls: 3 Days in Concord with Kids

3 Days · Young Families

Concord, Massachusetts

Little Women & Loon Calls: 3 Days in Concord with Kids

6 stops

Still Water, Deep Woods: 3 Days Solo at Quabbin Reservoir

3 Days · Solo

Quabbin Reservoir area, Massachusetts

Still Water, Deep Woods: 3 Days Solo at Quabbin Reservoir

6 stops

Water, Woods, and Wide-Open Sky: 3 Days at Quabbin Reservoir

3 Days · Teen Families

Quabbin Reservoir area, Massachusetts

Water, Woods, and Wide-Open Sky: 3 Days at Quabbin Reservoir

6 stops

Still Water, Quiet Company: 3 Days Alone at Quabbin

3 Days · Solo

Quabbin Reservoir area, Massachusetts

Still Water, Quiet Company: 3 Days Alone at Quabbin

6 stops

Deep Water, Old Towns: Three Days at Quabbin

3 Days · Teen Families

Quabbin Reservoir area, Massachusetts

Deep Water, Old Towns: Three Days at Quabbin

7 stops

Still Water, Small Feet: A Family Weekend at Quabbin

3 Days · Young Families

Quabbin Reservoir area, Massachusetts

Still Water, Small Feet: A Family Weekend at Quabbin

5 stops

Cliffside Light: A Slow Coastal Escape on Martha's Vineyard

3 Days · Teen Families

Martha’s Vineyard (off-season), Massachusetts

Cliffside Light: A Slow Coastal Escape on Martha's Vineyard

4 stops

Wind, Roses, and Whale Bones: 3 Days in Off-Season Nantucket

3 Days · Teen Families

Nantucket (off-season), Massachusetts

Wind, Roses, and Whale Bones: 3 Days in Off-Season Nantucket

4 stops

Salted Air & Old Secrets: 3 Days on Salem's Historic Shoreline

3 Days · Teen Families

North Shore (Salem area), Massachusetts

Salted Air & Old Secrets: 3 Days on Salem's Historic Shoreline

5 stops

Salt Air & Empty Shores: 3 Days Alone on Off-Season Nantucket

3 Days · Solo

Nantucket (off-season), Massachusetts

Salt Air & Empty Shores: 3 Days Alone on Off-Season Nantucket

6 stops

Dune Light & Quiet Company: 3 Days Solo on the Outer Cape

3 Days · Solo

Cape Cod (off-season), Massachusetts

Dune Light & Quiet Company: 3 Days Solo on the Outer Cape

5 stops

Cliff Light & Quiet Roads: A Solo Off-Season Escape to Martha's Vineyard

3 Days · Solo

Martha’s Vineyard (off-season), Massachusetts

Cliff Light & Quiet Roads: A Solo Off-Season Escape to Martha's Vineyard

5 stops

Dune Light & Quiet Shores: 3 Days in Off-Season Provincetown

3 Days · Teen Families

Cape Cod (off-season), Massachusetts

Dune Light & Quiet Shores: 3 Days in Off-Season Provincetown

6 stops

Salt Air & Shadowed Streets: Three Days Solo on the North Shore

3 Days · Solo

North Shore (Salem area), Massachusetts

Salt Air & Shadowed Streets: Three Days Solo on the North Shore

6 stops

Sand, Silence & Salt Air: 3 Days Alone on the Outer Cape

3 Days · Solo

Cape Cod (off-season), Massachusetts

Sand, Silence & Salt Air: 3 Days Alone on the Outer Cape

6 stops

Cliffside Solitude: 3 Days Alone with Martha's Vineyard's Western Light

3 Days · Solo

Martha’s Vineyard (off-season), Massachusetts

Cliffside Solitude: 3 Days Alone with Martha's Vineyard's Western Light

4 stops

Rose Lanes & Restless Tides: 3 Days in Nantucket for Families

3 Days · Teen Families

Nantucket (off-season), Massachusetts

Rose Lanes & Restless Tides: 3 Days in Nantucket for Families

4 stops

Cliffs, Light, and Salt Air: 3 Days on Martha's Vineyard

3 Days · Teen Families

Martha’s Vineyard (off-season), Massachusetts

Cliffs, Light, and Salt Air: 3 Days on Martha's Vineyard

5 stops

Salt Air & Solitude: 3 Days Alone on Nantucket

3 Days · Solo

Nantucket (off-season), Massachusetts

Salt Air & Solitude: 3 Days Alone on Nantucket

4 stops

Dune Light and Salt Air: 3 Days on the Outer Cape

3 Days · Teen Families

Cape Cod (off-season), Massachusetts

Dune Light and Salt Air: 3 Days on the Outer Cape

8 stops

Salted Air & Old Secrets: 3 Days on Salem's Historic Shore

3 Days · Teen Families

North Shore (Salem area), Massachusetts

Salted Air & Old Secrets: 3 Days on Salem's Historic Shore

5 stops

Salt Air & Old Secrets: Three Days Solo on Salem's Shore

3 Days · Solo

North Shore (Salem area), Massachusetts

Salt Air & Old Secrets: Three Days Solo on Salem's Shore

4 stops

Dune Light & Gallery Quiet: 3 Days at the Cape's Outer Edge

3 Days · Active Retirees

Cape Cod (off-season), Massachusetts

Dune Light & Gallery Quiet: 3 Days at the Cape's Outer Edge

4 stops

Rose Lanes & Salt Air: 3 Days in Nantucket

3 Days · Active Retirees

Nantucket (off-season), Massachusetts

Rose Lanes & Salt Air: 3 Days in Nantucket

6 stops

Salt Air & Old Stories: Three Days on Salem's Cobblestones

3 Days · Active Retirees

North Shore (Salem area), Massachusetts

Salt Air & Old Stories: Three Days on Salem's Cobblestones

3 stops

Clay Cliffs & Quiet Light: A Slow Western Escape on Martha's Vineyard

3 Days · Active Retirees

Martha’s Vineyard (off-season), Massachusetts

Clay Cliffs & Quiet Light: A Slow Western Escape on Martha's Vineyard

4 stops

Cliffside Quiet: 3 Days of Wildflowers and Sea Wind on Martha's Vineyard

3 Days · Young Families

Martha’s Vineyard (off-season), Massachusetts

Cliffside Quiet: 3 Days of Wildflowers and Sea Wind on Martha's Vineyard

4 stops

Gables, Gulls, and Gentle Museum Hours: 3 Days in Salem with Little Ones

3 Days · Young Families

North Shore (Salem area), Massachusetts

Gables, Gulls, and Gentle Museum Hours: 3 Days in Salem with Little Ones

3 stops

Dunes, Tide Pools & Quiet Galleries: 3 Days in Off-Season Cape Cod

3 Days · Young Families

Cape Cod (off-season), Massachusetts

Dunes, Tide Pools & Quiet Galleries: 3 Days in Off-Season Cape Cod

4 stops

Rose Lanes & Quiet Tides: 3 Days in Off-Season Nantucket

3 Days · Young Families

Nantucket (off-season), Massachusetts

Rose Lanes & Quiet Tides: 3 Days in Off-Season Nantucket

6 stops

Salted Air & Old Doorways: 3 Days on the North Shore

3 Days · Couples

North Shore (Salem area), Massachusetts

Salted Air & Old Doorways: 3 Days on the North Shore

5 stops

Showing 60 of 101 — explore all of Massachusetts.

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